Thioanisole → Methyl (3s,7as)-6-benzyloxycarbonylamino-5-oxohexahydropyrrolizine-3-carboxylate

HRID 10424

Reaction equation

[CH2:1]([O:8][C:9]([NH:11][CH:12]([C:30]([O:32]C)=O)[CH2:13][C@H:14]1[N:18](C(OC(C)(C)C)=O)[C@H:17]([C:26]([O:28][CH3:29])=[O:27])[CH2:16][CH2:15]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(SC)C=CC=CC=1>FC(F)(F)C(O)=O>[CH2:1]([O:8][C:9]([NH:11][CH:12]1[CH2:13][C@H:14]2[N:18]([C@H:17]([C:26]([O:28][CH3:29])=[O:27])[CH2:16][CH2:15]2)[C:30]1=[O:32])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 95 °C

Procedure

1500 mg of 1-tert-butyl 2-methyl (2S,5S)-5-(2-benzyloxycarbonylamino-2-methoxycarbonylethyl)pyrrolidine-1,2-dicarboxylate were mixed with 0.2 ml of thioanisole. Then 10 ml of trifluoroacetic acid were added, and the mixture was stirred for 45 min. The solvents were then removed in vacuo, and the residue was taken up in 10 ml of pyridine. 1.1 ml of diisopropylethylamine were added, and the mixture was heated at 95° C. for 3 h. The solvents were removed in vacuo, and the residue was chromatographed on silica gel.

Workup

customThe solvents were then removed in vacuo
addition1.1 ml of diisopropylethylamine were added
customThe solvents were removed in vacuo
customthe residue was chromatographed on silica gel

Sources & evidence

ORD record: ord-cb72a94ce0d34f9d96a25ac130802067
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07094800B2

Linked notes

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