HCID 86673837, compound → HCID 86673840, compound

HRID 1527392Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:12][C@:11]([CH2:14][N:15]=[N+:16]=[N-:17])([F:13])[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(OC(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])([F:13])[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])([CH3:2])[CH3:3]

Participants

Reactant 2

HCID 86673837HCID 86673837, compound

HCID 86673839HCID 86673839, compound

Product 1

HCID 86673840HCID 86673840, compound

Procedure

was obtained using the same protocols as described in Scheme B15 step A and B 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 (LC/MS): 474.1/476.2 [M+H]+, 472.1 [M−H]−; tR (HPLC conditions f): 2.180 min, 19F NMR (100 MHz, DMSO-d6) δ (ppm): −120, −150.

Workup

customwas obtained
custom2.180 min, 19F NMR (100 MHz, DMSO-d6) δ (ppm): −120, −150

Sources & evidence

ORD record: ord-fc31ff938cf845638e7bf622f5610db9
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09085555B2

Reaction notes

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