{(3S,4S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-methoxy-pyrrolidin-1-yl}-acetic acid ethyl ester → 2-(2-{(3S,4S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-methoxy-pyrrolidin-1-yl}-acetylamino)-6,7-dihydro-thiazolo[5,4-]pyridine-5-carboxylic acid tert-butyl ester

HRID 1162716Notes

Reaction equation

HRID 1162716 reaction equation
C(O[C:4](=[O:22])[CH2:5][N:6]1[CH2:10][C@H:9]([O:11][CH3:12])[C@@H:8]([NH:13][C:14]([C:16]2[S:17][C:18]([Cl:21])=[CH:19][CH:20]=2)=[O:15])[CH2:7]1)C.[C:23]([O:27][C:28]([C:30]1[CH2:35][CH2:34][C:33]2[S:36][C:37]([NH2:39])=[N:38][C:32]=2[N:31]=1)=[O:29])([CH3:26])([CH3:25])[CH3:24]>>[C:23]([O:27][C:28]([C:30]1[CH2:35][CH2:34][C:33]2[S:36][C:37]([NH:39][C:4](=[O:22])[CH2:5][N:6]3[CH2:10][C@H:9]([O:11][CH3:12])[C@@H:8]([NH:13][C:14]([C:16]4[S:17][C:18]([Cl:21])=[CH:19][CH:20]=4)=[O:15])[CH2:7]3)=[N:38][C:32]=2[N:31]=1)=[O:29])([CH3:26])([CH3:24])[CH3:25]

Participants

3

Reactant 2

HCID 58748327{(3S,4S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-methoxy-pyrrolidin-1-yl}-acetic acid ethyl esterHCID 866088402-Amino-6,7-dihydro-thiazolo[5,4]pyridine-5-carboxylic acid tert-butyl ester

Product 1

HCID 866088392-(2-{(3S,4S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-methoxy-pyrrolidin-1-yl}-acetylamino)-6,7-dihydro-thiazolo[5,4-]pyridine-5-carboxylic acid tert-butyl ester

Procedure

94.1 In analogy to example 25.3 {(3S,4S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-methoxy-pyrrolidin-1-yl}-acetic acid ethyl ester (example 25.2) was reacted with 2-amino-6,7-dihydro-thiazolo[5,4]pyridine-5-carboxylic acid tert-butyl ester (CAS 365996-05-0) to give 2-(2-{(3S,4S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-methoxy-pyrrolidin-1-yl}-acetylamino)-6,7-dihydro-thiazolo[5,4-]pyridine-5-carboxylic acid tert-butyl ester as off-white solid. MS 556.3 ([M+H]+)

Sources & evidence

ORD record
ord-27c1e994a6b54a89b36ed87eb2735d38
Source dataset
uspto-grants-2010_10
Patent number
US07820699B2

Reaction notes

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