HCID 86673837, compound → HCID 86673838, compound

HRID 1527391Notes

Reaction equation

HRID 1527391 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@:11]([CH2:14][N:15]=[N+:16]=[N-:17])(F)[CH2:10][C@H:9]1[C:18](=[O:29])[NH:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:22]=1[F:28])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O:34]C(N1C[C@@](O)(COS(C)(=O)=O)C[C@H]1C(=O)NCC1C=CC=C(Cl)C=1F)=O)(C)(C)C>>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@:11]([CH2:14][N:15]=[N+:16]=[N-:17])([OH:34])[CH2:10][C@H:9]1[C:18](=[O:29])[NH:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:22]=1[F:28])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 86673837HCID 86673837, compoundHCID 86673839HCID 86673839, compound

Product 1

HCID 86673838HCID 86673838, compound

Procedure

was obtained using the same protocols as described in Scheme B15 step A for the preparation of (2S,4R)-4-azidomethyl-2-(3-chloro-2-fluoro-benzylcarbamoyl)-4-fluoro-pyrrolidine-1-carboxylic acid tert-butyl ester starting from (2S,4R)-2-(3-chloro-2-fluoro-benzylcarbamoyl)-4-hydroxy-4-methanesulfonyloxy methyl-pyrrolidine-1-carboxylic acid tert-butyl ester (prepared from (2S,4R)-2-(3-chloro-2-fluoro-benzylcarbamoyl)-4-hydroxy-4-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester as described scheme B13). MS (UPLC/MS): 450/452 [M+Na]+, 472/474 [M+HCOO]−; tR (HPLC conditions f): 2.08 min.

Workup

  1. customwas obtained
  2. custom2.08 min.

Sources & evidence

ORD record
ord-b4d58822044c473c8a415cd06a23d57b
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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