Cyclobutanecarboxylic acid → Methyl (3s)-3-[(cyclobutylcarbonyl)amino]-3-phenylpropanoate

HRID 1635957Notes

Reaction equation

HRID 1635957 reaction equation
[NH2:1][C@H:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:3][C:4]([O:6][CH3:7])=[O:5].[CH:14]1([C:18](O)=[O:19])[CH2:17][CH2:16][CH2:15]1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[CH:14]1([C:18]([NH:1][C@H:2]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:3][C:4]([O:6][CH3:7])=[O:5])=[O:19])[CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 19494Cyclobutanecarboxylic acidHCID 81531DiisopropylethylamineHCID 788099Methyl (S)-3-amino-3-phenylpropanoate

Product 1

HCID 29912481Methyl (3s)-3-[(cyclobutylcarbonyl)amino]-3-phenylpropanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the amino ester from Example 6, Step A (4.2 mmol, 896 mg) and cyclobutanecarboxylic acid (5.0 mmol, 476 μL) in 10 mL of DCM containing N,N-diisopropylethylamine (12.5 mmol, 2.17 mL) was added 1-(3-dimethylamino)propyl-3-ethylcarbodiimide hydrochloride (5.0 mmol, 958 mg). After 16 h the reaction mixture was washed with H2O (10 mL), 1 M citric acid (10 mL) and saturated NaHCO3 (10 mL). The organic phase was dried with MgSO4 and the solvent removed under reduced pressure to afford the product as a white solid. MS (ESI): m/z 485 (M+H). HPLC B: 1.58 min.

Workup

  1. washAfter 16 h the reaction mixture was washed with H2O (10 mL), 1 M citric acid (10 mL) and saturated NaHCO3 (10 mL)
  2. dry with materialThe organic phase was dried with MgSO4
  3. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-e167106ae04442b8b0248e08e36dc395
Source dataset
uspto-grants-2003_01
Patent number
US06511994B2

Reaction notes

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