Triethylamine → HCID 25136280, compound

HRID 1353631Notes

Reaction equation

HRID 1353631 reaction equation
[CH3:1][O:2][C:3](=[O:25])[C@H:4]([NH:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[C:8]([NH2:13])[CH:7]=1.C(N(CC)CC)C.[C:33](N1C=CN=C1)(N1C=CN=C1)=[O:34]>O1CCCC1>[CH3:1][O:2][C:3]([C@H:4]([NH:14][C:15](=[O:16])[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]2[NH:12][C:33](=[O:34])[NH:13][C:8]=2[CH:7]=1)=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 25135868HCID 25135868, compound

Product 1

HCID 25136280HCID 25136280, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a dilute solution of (R)-2-benzyloxycarbonylamino-3-(3,4-diamino-phenyl)-propionic acid methyl ester (600 mg, 1.44 mmol) in tetrahydrofuran (125 mL) was added triethylamine (320 mg, 3.17 mmol) followed by 1,1′-carbonyldiimidazole (280 mg, 1.73 mmol). The reaction mixture was stirred at room temperature for 16 h and then filtered to remove solid. The filtrate was evaporated and subjected to flash column chromatography (1:12 methanol/methylene chloride) to give the title compound (313 mg, 59% yield). 1H-NMR (CD3OD, 300 MHz) δ 7.28–7.21 (m, 5H), 6.94–6.83 (m, 3H), 5.06–4.95 (m, 2H), 4.46–4.41 (m, 1H), 3.68 (s, 3H), 3.17–3.11 (m, 1H), 2.95–2.88 (m, 1H). LC/MS: tR=2.11 min, 370 (MH)+.

Workup

  1. filtrationfiltered
  2. customto remove solid
  3. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-ab611a198e38453187e637ac8e3c4401
Source dataset
uspto-grants-2007_05
Patent number
US07220862B2

Reaction notes

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