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

HRID 10424

반응식

HRID 10424 반응식
[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

참가 물질

4

반응물 2

HCID 7520ThioanisoleHCID 1317258971-Tert-butyl 2-methyl (2s,5s)-5-(2-benzyloxycarbonylamino-2-methoxycarbonylethyl)pyrrolidine-1,2-dicarboxylate

생성물 1

HCID 91509044Methyl (3s,7as)-6-benzyloxycarbonylamino-5-oxohexahydropyrrolizine-3-carboxylate

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

반응 조건

온도
95 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-cb72a94ce0d34f9d96a25ac130802067
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094800B2

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