Triethylamine → HCID 131723447, compound

HRID 2304860Notes

Reaction equation

HRID 2304860 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].Cl.[CH3:22][O:23][C:24](=[O:29])[C@H:25]([CH2:27][OH:28])[NH2:26].CCN=C=NCCCN(C)C.C(N(CC)CC)C>C(Cl)Cl.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].[CH3:22][O:23][C:24](=[O:29])[C@H:25]([CH2:27][OH:28])[NH2:26]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)HCID 2755954Boc-D-homophenylalanine

Product 1

HCID 131723447HCID 131723447, compoundYield 91.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-Boc-D-homophenylalanine (1.0 g) was coupled with L-serine methyl ester hydrochloride (600 mg) with EDAC (892 mg) and triethylamine (650 μL) in methylene chloride (15 mL). After stirring for 10 h., the reaction mixture is poured into ethyl acetate, washed successively with water, 1 N hydrochloric acid, sat aqueous bicarbonate and brine. The organic layer is dried (Na2SO4) and concentrated in vacuo to give the title compound (1.3 g) as a white solid: 1H NMR (400 MHz, CDCl3) δ 1.43 (s, 9H), 1.97 (m, 1H), 2.20 (m, 1H), 2.73 (m, 2H), 2.84 (m, 1H), 3.79 (s, 3H), 3.95 (m, 2H), 4.17 (m, 1H), 4.62 (m, 1H), 5.14 (bs, 1H, NH), 7.06 (bd, 1H, NH), 7.19 (m, 3H), and 7.28 (m, 2H).

Workup

  1. washwashed successively with water, 1 N hydrochloric acid
  2. dry with materialThe organic layer is dried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-716c15681eb24440a8b8328a5ecb4e6b
Source dataset
uspto-grants-2002_08
Patent number
US06436980B1

Reaction notes

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