Methanol → HCID 178500461, compound

HRID 877171Notes

Reaction equation

S(Cl)([Cl:3])=O.C(OC([NH:12][C@@H:13]1[CH2:18][CH2:17][C@H:16]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])[CH2:15][CH2:14]1)=O)(C)(C)C.[CH3:24]O>>[ClH:3].[NH2:12][C@@H:13]1[CH2:14][CH2:15][C@H:16]([CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH2:17][CH2:18]1

Participants

Reactant 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 178453887HCID 178453887, compound

Product 1

HCID 178500461HCID 178500461, compound

Procedure

At −5° C., 2.9 ml (40.5 mmol) of thionyl chloride were slowly added dropwise to 100 ml of methanol, and the mixture was stirred at this temperature for 10 min. 5 g (18.4 mmol) of 3-{cis-4-[(tert-butoxycarbonyl)amino]cyclohexyl}propanoic acid were then added in one portion, and the reaction mixture was stirred at room temperature overnight. After the reaction had gone to completion, the solvent was evaporated under reduced pressure. This gave 3.95 g (17.8 mmol, 96.7% of theory) of a colorless solid.

Workup

stirringthe reaction mixture was stirred at room temperature overnight
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-427b4e9da7594f139ae427d351fe177b
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987256B2

Reaction notes

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