3,3-Dimethylbutanal → 2-Benzyloxycarbonylamino-5,5-dimethyl-hex-2-enoic acid methyl ester

HRID 1060659

反応式

HRID 1060659 の反応式
[CH3:1][O:2][C:3]([CH:5](P(OC)(OC)=O)[NH:6][C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])=[O:4].[C:23]([CH2:27][CH:28]=O)([CH3:26])([CH3:25])[CH3:24].C1CCN2C(=NCCC2)CC1>C1COCC1.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:4])[C:5]([NH:6][C:7]([O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:8])=[CH:28][CH2:27][C:23]([CH3:26])([CH3:25])[CH3:24]

参加物

6

反応物 3

HCID 763353,3-DimethylbutanalHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2734718Methyl 2-{[(benzyloxy)carbonyl]amino}-2-(dimethyl phosphono)acetate

生成物 1

HCID 694337082-Benzyloxycarbonylamino-5,5-dimethyl-hex-2-enoic acid methyl ester収率 94.4%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

N-(Benzyloxycarbonyl)-α-phosphonoglycine trimethyl ester (2 g, 6.0 mmol, 1.0 equiv) was dissolved in dry THF (20 mL). tert-Butylacetaldehyde (0.758 mL, 6.0 mmol, 1.0 equiv) and DBU (0.903 mL, 6.0 mmol, 1.0 equiv) were added and the reaction mixture was stirred for 16 h. The solution was diluted with 100 mL of CH2Cl2 and washed with 1×50 mL water, and 1×50 mL brine. The organic layer was dried over Na2SO4, decanted and concentrated in vacuo to provide 2-benzyloxycarbonylamino-5,5-dimethyl-hex-2-enoic acid methyl ester as a thick oil (1.73 g, 94%) which was used without further purification; MS: 306 (M+1).

後処理

  1. washwashed with 1×50 mL water, and 1×50 mL brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customdecanted
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-d72b7a84bb3d4ffca02c6e298284073a
出典データセット
uspto-grants-2003_02
特許番号
US06525052B2

関連ノート

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