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

HRID 852541ノート

反応式

HRID 852541 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-74ff8ebf089b454ea9e954cecdde9c38
出典データセット
uspto-grants-2007_08
特許番号
US07253198B2

反応ノート

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