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

HRID 1060659Notes

Reaction equation

HRID 1060659 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-d72b7a84bb3d4ffca02c6e298284073a
Source dataset
uspto-grants-2003_02
Patent number
US06525052B2

Reaction notes

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