N-(tert-Butoxycarbonyl)-L-cysteine methyl ester → HCID 66836001, compound

HRID 572887Notes

Reaction equation

HRID 572887 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]([O:18][CH:19]2[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]2)[C:9]2[NH:13][C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:26][O:27][C:28](=[O:40])[C@H:29]([CH2:38][SH:39])[NH:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32]>>[CH3:26][O:27][C:28](=[O:40])[CH:29]([NH:30][C:31]([O:33][C:34]([CH3:36])([CH3:35])[CH3:37])=[O:32])[CH2:38][S:39][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]([C:9]2[NH:13][C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[N:10]=2)[O:18][CH:19]2[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]2)[CH:3]=1

Participants

3

Reactant 2

HCID 10977409N-(tert-Butoxycarbonyl)-L-cysteine methyl esterHCID 56947989HCID 56947989, compound

Product 1

HCID 66836001HCID 66836001, compound

Procedure

The compound is synthesized from 2-[(3-bromophenyl)(1-methylpiperidin-4-yloxy)methyl]-1H-benzimidazole (example 72A) and N-Boc-Cysteine methyl ester using the method described in example 150; mixture of diastereomers. 1H NMR: 10.66 and 9.83 (sl, 1H), 7.90-7.70 (m, 2H), 7.50-7.35 (m, 2H), 7.35-7.18 (m, 5H), 5.87 and 5.85 (s, 1H), 5.58-5.30 (m, 1H), 4.65-4.40 (m, 1H), 3.70-3.20 (m, 6H), 2.82-2.62 (m, 2H), 2.28 and 2.26 (s, 3H), 2.22-1.65 (m, 6H), 1.53 and 1.45 (s, 9H).

Workup

  1. additionmixture of diastereomers

Sources & evidence

ORD record
ord-a60d5cc8ca024d4f961beef7e65e41fc
Source dataset
uspto-grants-2015_05
Patent number
US09029357B2

Reaction notes

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