Acetic Acid → HCID 87830596, compound

HRID 1006842Notes

Reaction equation

[CH2:1]([O:8][CH2:9][C@H:10]1[N:14]([S:15]([C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=2)(=[O:17])=[O:16])[CH2:13][C@@H:12]([S:28]C(=O)C)[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].C(O)(=O)C>CO>[CH2:1]([O:8][CH2:9][C@H:10]1[N:14]([S:15]([C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=2)(=[O:16])=[O:17])[CH2:13][C@@H:12]([SH:28])[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

S-Acetyl deprotection: To a solution of (3S,5S)-thioacetic acid S-[5-benzyloxymethyl-1-(naphthalene-2-sulfonyl)-pyrrolidin-3-yl] ester (1.2 g) in methanol (17 ml) was added sodium methanolate (28%-solution in methanol, 0.55 ml) at 0° C. The reaction mixture was stirred at 0° C. for 1.5 h, and acetic acid (0.17 ml) was added. The reaction mixture was concentrated, and the residue was extracted with EtOAc. The organic phases were washed with water, dried over magnesium sulphate and concentrated. The residue was chromatographed on silica gel using EtOAc/hexane 1:3 and 1:2 as eluents to obtain (3S,5S)-5-benzyloxymethyl-1-(naphthalene-2-sulfonyl)-pyrrolidine-3-thiol (0.59 g) as a slightly coloured syrup, MS: 414 (MH+).

Workup

concentrationThe reaction mixture was concentrated
extractionthe residue was extracted with EtOAc
washThe organic phases were washed with water
dry with materialdried over magnesium sulphate
concentrationconcentrated
customThe residue was chromatographed on silica gel

Sources & evidence

ORD record: ord-8acd36de8e8d4f7091b11997be96b2b6
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06790860B2

Reaction notes

Loading…