Dichloromethane → dimethyl (2R)-2-amino-12-carboxy-4-thia-1,13-tridecanedicarboxylate hydrochloride

HRID 5415Notes

Reaction equation

[NH2:1][C@@H:2]([CH2:8][S:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]([C:23]([O:25]C(C)(C)C)=[O:24])[CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH2:3][C:4]([O:6][CH3:7])=[O:5].C(Cl)[Cl:31]>>[ClH:31].[NH2:1][C@@H:2]([CH2:8][S:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]([C:23]([OH:25])=[O:24])[CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH2:3][C:4]([O:6][CH3:7])=[O:5]

Participants

Reactant 2

HCID 6344Dichloromethane

HCID 54385278HCID 54385278, compound

Product 1

HCID 86747212dimethyl (2R)-2-amino-12-carboxy-4-thia-1,13-tridecanedicarboxylate hydrochloride

Procedure

Dimethyl (2R)-2-amino-12-t-butoxycarbonyl-4-thia-1,13-tridecanedicarboxylate (3.39 g, 8.36 mmol) is dissolved in methylene chloride (50 ml) and hydrogen chloride gas is bubbled through the solution for 5 minutes. The reaction mixture is stirred for 2 hours at room temperature. The solvent is evaporated to give dimethyl (2R)-2-amino-12-carboxy-4-thia-1,13-tridecanedicarboxylate hydrochloride as an oil.

Workup

customhydrogen chloride gas is bubbled through the solution for 5 minutes
customThe solvent is evaporated

Sources & evidence

ORD record: ord-13270cd53a13413d86e4aa414a30ff1f
Source dataset: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05244889

Reaction notes

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