Triethylamine → HCID 73294496, compound

HRID 530472Notes

Reaction equation

HRID 530472 reaction equation
CCN(CC)CC.O[C@@H:9]([CH3:27])[C@@H:10]([NH:14][C:15]([O:17][CH2:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:16])[C:11]([OH:13])=[O:12].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[C:21]1([CH2:20][CH2:19][CH2:18][O:17][C:15](=[O:16])[NH:14][C@H:10]2[C:11](=[O:13])[O:12][C@H:9]2[CH3:27])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86699911HCID 86699911, compound

Product 1

HCID 73294496HCID 73294496, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In a four necked round bottom flask, Et3N (1.4 ml, 10.1 mmol) was added to a solution of (2R,3S)-3-hydroxy-2-{[(3-phenylpropoxy)carbonyl]amino}butanoic acid (0.95 g, 3.38 mmol) in dry CH2Cl2 (40 mL) under argon. After cooling at 0° C., HBTU (1.92 g, 5.07 mmol, 1.5 eq) was added and the mixture stirred 3 h at 0° C., then 16 h at rt. The obtained solid was filtered off and the solvent removed under vacuum. The crude was purified by typical silica gel column chromatography, eluting with Cy/AcOEt (from 95:5 to 60:40). The resulting white solid (0.280 g) was further triturated with cyclohexane to afford the pure title compound (0.240 g, 31%), as white solid. MS (ESI) m/z: 262.27 [M−H]−. Rf=0.29 (Cy/EtOAc 8:2; detection: phosphomolybdic acid). FTIR (cm−1): 3328, 3064, 3030, 2972, 2929, 2859, 1851, 1691, 1542, 1333, 1270, 1130, 1083, 1024, 843, 822, 697. 1H NMR (CDCl3): δ 1.46 (d, 3H); 1.93-2.00 (m, 2H); 2.67-2.71 (m, 2H); 4.09-4.18 (m, 2H); 4.84-4.90 (m, 1H); 5.38-5.48 (m, 2H); 7.11-7.31 (m, 5H).

Workup

  1. custom16 h
  2. customat rt
  3. filtrationThe obtained solid was filtered off
  4. customthe solvent removed under vacuum
  5. customThe crude was purified by typical silica gel column chromatography
  6. washeluting with Cy/AcOEt (from 95:5 to 60:40)
  7. customThe resulting white solid (0.280 g) was further triturated with cyclohexane

Sources & evidence

ORD record
ord-496691d0ee484c86987506ff84aecf61
Source dataset
uspto-grants-2016_05
Patent number
US09353075B2

Reaction notes

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