Methyl chloroformate → (R)-methyl 5-bromo-1-((5-((2-ethoxy-2-oxoethyl)thio)thiazol-2-yl)carbamoyl)spiro[indoline-3,3'-pyrrolidine]-1'-carboxylate

HRID 1411275Notes

Reaction equation

HRID 1411275 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C@:10]3([CH2:14][CH2:13][N:12]([C:15]([O:17][C:18](C)(C)C)=[O:16])[CH2:11]3)[CH2:9][NH:8][C:5]2=[CH:6][CH:7]=1.[NH2:22][C:23]1[S:24][C:25]([S:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:26][N:27]=1.Cl.NC1SC(Cl)=CN=1.Cl[C:44](OC)=[O:45]>>[Br:1][C:2]1[CH:3]=[C:4]2[C@:10]3([CH2:14][CH2:13][N:12]([C:15]([O:17][CH3:18])=[O:16])[CH2:11]3)[CH2:9][N:8]([C:44](=[O:45])[NH:22][C:23]3[S:24][C:25]([S:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:26][N:27]=3)[C:5]2=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 6586Methyl chloroformateHCID 1487432-Amino-5-chlorothiazole hydrochlorideHCID 21455623Ethyl 2-(2-aminothiazol-5-ylthio)acetateHCID 90449881(R)-t-butyl 5-bromospiro[indoline-3,3'-pyrrolidine]-1'-carboxylate

Product 1

HCID 90449381(R)-methyl 5-bromo-1-((5-((2-ethoxy-2-oxoethyl)thio)thiazol-2-yl)carbamoyl)spiro[indoline-3,3'-pyrrolidine]-1'-carboxylate

Procedure

The captioned compound was obtained in the form of a white solid by performing the same reactions and/or treatments as those in Examples 1, 2, and 3, with the exceptions that (R)-t-butyl 5-bromospiro[indoline-3,3′-pyrrolidine]-1′-carboxylate was used instead of t-butyl 5-bromospiro[indoline-3,3′-pyrrolidine]-1′-carboxylate, that the ethyl 2-((2-aminothiazol-5-yl)thio)acetate synthesized by a method described in the known methods (International Publication WO2005/066145 etc.) was used instead of 2-amino-5-chlorothiazole hydrochloride, and that methyl chloroformate was used instead of acetyl chloride.

Workup

  1. customThe captioned compound was obtained in the form of a white solid
  2. customsynthesized by a method

Sources & evidence

ORD record
ord-367c894a5d7b48b4be03449d99ef4f7d
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

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