Triethylamine → HCID 68234999, compound

HRID 1907149Notes

Reaction equation

HRID 1907149 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:11]([OH:13])=O)[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:14][CH2:15][C@@H:16]([NH:24][C:25](=[O:34])[O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C.O>[CH2:17]([C@H:16]([NH:24][C:25](=[O:34])[O:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[CH2:15][NH:14][C:11](=[O:13])[C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH3:10])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 637606BOC-D-alanineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 15030820HCID 15030820, compound

Product 1

HCID 68234999HCID 68234999, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(tert-butoxycarbonyl)-D-alanine (595 mg, 3.14 mmol) in DMF (20 mL) was added benzyl [(1S)-2-amino-1-benzylethyl]carbamate (Tet. Lett. 2005, 46(41), 7069) (968 mg, 3.30 mmol), HBTU (1.43 g, 3.77 mmol) and triethylamine (1.8 ml, 12.6 mmol) at room temperature. After stirring the reaction mixture for 15 hours, water (20 mL) was added to the mixture. The mixture was extracted with ethyl acetate/heptane 5/1 (2×20 mL) and the combined extracts were washed with 1N citric acid (20 mL), saturated aqueous sodium bicarbonate (20 mL) and brine (20 mL). The organic layer was dried over sodium sulfate, and concentrated under reduced pressure to afford the title compound as a white solid in 99% yield, 1.42 g. 1H NMR (400 MHz, CDCl3) : 1.24 (d, 3H), 1.43 (s, 9H), 2.59-2.86 (m, 4H), 3.13-3.25 (m, 2H), 3.34-3.44 (m, 1H), 3.89-4.05 (m, 2H), 4.90-5.05 (m, 2H), 7.11-7.36 (m, 10H).

Workup

  1. extractionThe mixture was extracted with ethyl acetate/heptane 5/1 (2×20 mL)
  2. washthe combined extracts were washed with 1N citric acid (20 mL), saturated aqueous sodium bicarbonate (20 mL) and brine (20 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-629cd44bb69541debb796f5aca353639
Source dataset
uspto-grants-2013_12
Patent number
US08598123B2

Reaction notes

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