Toluene tert-butyl alcohol → {5-(Benzyloxycarbonylamino-methyl)-2-[4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-2-oxo-piperazin-1-ylmethyl]-thiazol-4-yl}-acetic acid ethyl ester

HRID 1433081Notes

Reaction equation

HRID 1433081 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8]([S:10]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][C:20]([NH2:22])=[S:21])[CH2:15][CH2:14]3)(=[O:12])=[O:11])[S:7][C:6]=2[CH:23]=1.[CH2:24]([O:26][C:27](=[O:45])[CH2:28][C:29](=O)[CH:30](Br)[CH2:31][NH:32][C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34])[CH3:25].C1(C)C=CC=CC=1.C([OH:57])(C)(C)C>>[CH2:24]([O:26][C:27](=[O:45])[CH2:28][C:29]1[N:22]=[C:20]([CH2:19][N:16]2[CH2:17][CH2:18][N:13]([S:10]([C:8]3[S:7][C:6]4[CH:23]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=4[CH:9]=3)(=[O:11])=[O:12])[CH2:14][C:15]2=[O:57])[S:21][C:30]=1[CH2:31][NH:32][C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34])[CH3:25]

Participants

4

Reactant 3

HCID 22595558Toluene tert-butyl alcoholHCID 865925602-[4-(6-Chloro-benzo[b]thiophene-2-sulfonyl)-piperazin-1-yl]-thioacetamideHCID 865925625-Benzyloxycarbonylamino-4-bromo-3-oxo-pentanoic acid ethyl ester

Product 1

HCID 69026982{5-(Benzyloxycarbonylamino-methyl)-2-[4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-2-oxo-piperazin-1-ylmethyl]-thiazol-4-yl}-acetic acid ethyl ester

Procedure

A suspension of 2-[4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-piperazin-1-yl]-thioacetamide (200 mg, 0.5 mmol) and 5-benzyloxycarbonylamino-4-bromo-3-oxo-pentanoic acid ethyl ester (370 mg, 1.0 mmol) is heated at 90° C. in a mixture of toluene/t-butanol, 1:1 (5 mL) for 16 h. The reaction is concentrated and purified using column chromatography (silica, 2%MeOH/CH2Cl2) to provide {5-(benzyloxycarbonylamino-methyl)-2-[4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-2-oxo-piperazin-1-ylmethyl]-thiazol-4-yl}-acetic acid ethyl ester. 1H NMR (300 MHz, CDCl3) δ 7.87-7.81 (m, 3H), 7.45 (dd, 1H), 7.32 (s, 5H), 7.45 (bt, 1H), 5.07 (s, 2H), 4.73 (s, 2H), 4.42 (d, 2H), 4.13 (q, 2H), 3.90 (s, 2H), 3.76 (s, 2H), 3.61-3.55 (m, 2H), 3.50-3.43 (m, 2H), 1.24 (t, 3H); MS (ion spray) 677 (M+H)+.

Workup

  1. concentrationThe reaction is concentrated
  2. custompurified

Sources & evidence

ORD record
ord-59f64de916824feeb5c0ef40c85c8a15
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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