Triphenylphosphine → 3-(3-Benzyloxy-propoxy)-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester

HRID 852541노트

반응식

HRID 852541 반응식
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])[CH:7]=[C:6]([OH:16])[CH:5]=1.[CH2:18]([O:25][CH2:26][CH2:27][CH2:28]O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])[CH:7]=[C:6]([O:16][CH2:28][CH2:27][CH2:26][O:25][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:5]=1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 3479713-Benzyloxy-1-propanolHCID 5462977Diethyl azodicarboxylateHCID 22252977Methyl 3-hydroxy-5-(2-oxopyrrolidin-1-yl)benzoate

생성물 1

HCID 693568053-(3-Benzyloxy-propoxy)-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 3-hydroxy-5-(2-oxopyrrolidin-1-yl)-benzoic acid methyl ester (D37) (300 mg, 1.28 mmol, 1 equiv), 3-benzyloxypropan-1-ol (0.28 ml, 1.79 mmol, 1.4 equiv) and triphenyl phosphine (470 mg, 1.79 mmol, 1.4 equiv) in THF (10 ml) at room temperature was treated dropwise with DEAD (0.282 ml, 1.79 mmol, 1.4 equiv). The mixture was stirred for 16 h at room temperature then concentrated in vacuo. Purification by flash chromatography on silica gel (ethyl acetate/iso-hexane: 1/4 to 1/1) gave 3-(3-benzyloxy-propoxy)-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester (D38).

후처리

  1. concentrationthen concentrated in vacuo
  2. customPurification by flash chromatography on silica gel (ethyl acetate/iso-hexane: 1/4 to 1/1)

출처 및 근거

ORD 기록
ord-74ff8ebf089b454ea9e954cecdde9c38
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253198B2

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