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

HRID 25261

Reaction equation

HRID 25261 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-b21259ade78c46cb91e2d6a90cf23b15
Source dataset
uspto-grants-2005_02
Patent number
US06858623B2

Linked notes

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