Triethylamine → HCID 131723446, compound

HRID 2304857Notes

Reaction equation

HRID 2304857 reaction equation
[C:1]([NH:8][C@@H:9]([C:18]([OH:20])=[O:19])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.ClC(OCC)=O.Cl.[CH2:35]([O:37][C:38](=[O:43])[C@H:39]([CH2:41][OH:42])[NH2:40])[CH3:36]>ClCCl.C(OCC)(=O)C>[C:1]([NH:8][C@@H:9]([C:18]([OH:20])=[O:19])[CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)([O:3][C:4]([CH3:5])([CH3:7])[CH3:6])=[O:2].[CH2:35]([O:37][C:38](=[O:43])[C@H:39]([CH2:41][OH:42])[NH2:40])[CH3:36]

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 10928Ethyl chloroformateHCID 2724185L-Serine, ethyl ester, hydrochloride (1:1)HCID 2755954Boc-D-homophenylalanine

Product 1

HCID 131723446HCID 131723446, compoundYield 83.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A cold (0° C.) solution of N-Boc-D-homophenylalanine (300 mg) in dichloromethane (10 mL), under nitrogen atmosphere, was treated sequentially with triethylamine (165 μL) and ethyl chloroformate (102 μL). After stirring for 2 h at 0 C, the crude mixed anhydride was added dropwise to a solution of L-serine ethyl ester hydrochloride (182 mg), triethylamine (300 μL), and dichloromethane (2 mL). The mixture is stirred at 0° C. for 1 h and then allowed to warn to 25° C. and stirred for 12 h. The reaction mixture is diluted with ethyl acetate, washed successively with water and brine, dried (Na2SO4) and concentrated. The residue was purified using chromatography over silica gel (50% ethyl acetate/hexane) to afford the title compound (371 mg): 1H NMR (400 MHz, CDCl3) δ 1.32 (t, J=9.8 Hz, 3H), 1.46 (s, 9H), 1.97 (m, 1H), 2.11 (m, 1H), 2.75 (t, J=10.4 Hz, 2H), 3.97 (m, 2H), 4.14 (m, 1H), 4.25 (q, J=9.8 Hz, 2H), 4.60 (m, 1H), and 7.18-7.29 (m, 5H).

Workup

  1. stirringThe mixture is stirred at 0° C. for 1 h
  2. customto warn to 25° C.
  3. stirringstirred for 12 h
  4. washwashed successively with water and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified

Sources & evidence

ORD record
ord-f764a04207484572b8afc6d5c0407c79
Source dataset
uspto-grants-2002_08
Patent number
US06436980B1

Reaction notes

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