Oxalyl chloride → Dicyclohexylcarbodiimide

HRID 11171Notes

Reaction equation

C([C@H](NC([C:34]1[C:35]2C=[CH:37][NH:38][C:39]=2[CH:40]=[CH:41][CH:42]=1)=O)[C@H](O)C(N1[C@H](C(=O)NCC2C=CC=CC=2C)C(C)(C)SC1)=O)C1C=CC=CC=1.[C:43](Cl)(=O)[C:44](Cl)=O>>[CH2:44]1[CH2:43][CH2:40][CH:39]([N:38]=[C:37]=[N:38][CH:39]2[CH2:35][CH2:34][CH2:42][CH2:41][CH2:40]2)[CH2:35][CH2:34]1

Participants

Reactant 2

HCID 65578Oxalyl chloride

HCID 514529(4R)-3-[(2S,3S)-2-hydroxy-3-(1H-indole-4-carbonylamino)-4-phenyl-butanoyl]-5,5-dimethyl-N-(o-tolylmethyl)thiazolidine-4-carboxamide

Product 1

HCID 10868Dicyclohexylcarbodiimide

Procedure

The synthesis of compounds with the general structure 27 is as follows. The boc-protected thiazolidine carboxylic acid 1 is converted to amino-ketones 26 with requisite grignard reagents 25 in the presence of oxalyl chloride. Final compounds 27 are obtained by a DCC-mediated coupling of 26 and 4 followed by deprotection of the P2 phenol. Final compounds were purified either by flash chromatography or preparative HPLC. Specific Method D

Workup

customThe synthesis of compounds with the general structure 27

Sources & evidence

ORD record: ord-d385b842dcb8486f8120e8156d84ee72
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07094909B2

Reaction notes

Loading…