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Semicontinuous Process for GMP Manufacture of a Carbapenem Intermediate via Carbene Insertion Using an Immobilized Rhodium Catalyst

By Gage, James R.; Chen, Furong; Dong, Changming; Gonzalez, Miguel A.; Jiang, Yong; Luo, Yong; McLaws, Mark D.; Tao, Jian

View Resource (DOI)

Category

Peer-reviewed journal

Published on CMKC

Abstract

A two-stage flow process for cGMP manufacture of a commercially important carbapenem intermediate was developed. Stage 1 featured an intramolecular N–H insertion reaction catalyzed by an immobilized rhodium catalyst. In stage 2, phosphorylation of the resulting keto ester intermediate afforded the target, which was isolated in batch mode. The equipment design and process control strategy leading to validation of the process at the 100 kg scale are discussed.

Journal

Organic Process Research & Development. Volume 24, 2020, 2025–2033

DOI

10.1021/acs.oprd.0c00133

Type of publication

Peer-reviewed journal

Affiliations

  • Asymchem Inc.
  • Asymchem Life Science (Tianjin) Co., Ltd.

Article Classification

Research Article

Classification Areas

  • Intermediate

Tags

  1. Carbapenem
  2. dirhodium(II) immobilization
  3. Intermediate
  4. Post-translational modification
  5. Research Article
  6. Rhodium