Ethyl Acetate → 2-{[(Benzyloxy)carbonyl]amino}-3-(3-{[(t-butoxycarbonyl)amino]methyl}-4-methoxyphenyl)-2-propenoic acid methyl ester

HRID 1296218

Reaction equation

HRID 1296218 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([O:18][CH3:19])=[C:7]([CH:17]=1)[CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=O.[CH2:20]([O:27][C:28]([NH:30][CH:31](P(OC)(OC)=O)[C:32]([O-:34])=[O:33])=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[CH2:41]1CCN2C(=NCCC2)CC1.C(OCC)(=O)C>ClCCl>[CH3:41][O:34][C:32](=[O:33])[C:31]([NH:30][C:28]([O:27][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:29])=[CH:1][C:3]1[CH:4]=[CH:5][C:6]([O:18][CH3:19])=[C:7]([CH2:8][NH:9][C:10]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:16])[CH:17]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 22493931Tert-butyl (5-formyl-2-methoxybenzyl)carbamateHCID 131726531[(Benzyloxy)carbonyl]amino-2-(dimethoxyphosphoryl)acetate

Product 1

HCID 694858062-{[(Benzyloxy)carbonyl]amino}-3-(3-{[(t-butoxycarbonyl)amino]methyl}-4-methoxyphenyl)-2-propenoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.65 g of t-butyl N-(5-formyl-2-methoxybenzyl)carbamate, 3.81 g of methyl 2-([(benzyloxy)carbonyl]amino-2-(dimethoxyphosphoryl)acetate and 1.75 g of 1,8-diazabicyclo[5,4,0]-7-undecene were dissolved in 50 ml of dichloromethane, followed by stirring for 15 hours at room temperature. 300 ml of ethyl acetate was added, and the organic layer was successively washed with 150 ml of water and 150 ml of brine, dried over magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography, and 4.09 g of 2-{[(benzyloxy)carbonyl]amino}-3-(3-{[(t-butoxycarbonyl)amino]methyl}-4-methoxyphenyl)-2-propenoic acid methyl ester was obtained as a colorless solid.

Workup

  1. washthe organic layer was successively washed with 150 ml of water and 150 ml of brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0477333a245b4dbf88326acc3540545d
Source dataset
uspto-grants-2007_07
Patent number
US07244861B2

Linked notes

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