Triethylamine → HCID 86699918, compound

HRID 530481Notes

Reaction equation

HRID 530481 reaction equation
CCN(CC)CC.O[C@@H:9]([CH3:32])[C@@H:10]([NH:14][C:15]([O:17][CH:18]1[CH2:23][CH2:22][N:21]([C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:25])[CH2:20][CH2:19]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:24]([N:21]1[CH2:22][CH2:23][CH:18]([O:17][C:15](=[O:16])[NH:14][C@H:10]2[C:11](=[O:12])[O:13][C@H:9]2[CH3:32])[CH2:19][CH2:20]1)(=[O:25])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86699919HCID 86699919, compound

Product 1

HCID 86699918HCID 86699918, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In a four necked round bottom flask, under Argon atmosphere, Et3N (1.2 mL, 8.56 mmol) was added to a solution of (2R,3S)-3-hydroxy-2-[({[1-(phenylcarbonyl)piperidin-4-yl]oxy}carbonyl)amino]-butanoic acid (1.0 g, 2.85 mmol) in dry CH2Cl2 (40 mL). After cooling at 0° C., HBTU (1.62 g, 4.28 mmol) was added and the mixture stirred 3 h at 0° C., then 16 h at rt. The solvent was removed under vacuum, and the resulting crude mixture was purified by column chromatography using a Teledyne ISCO apparatus, eluting with CH2Cl2/AcOEt (50:50). The resulting yellow solid was further purified trough reverse-phase automatic column chromatography, eluting with H2O/CH3CN (70:30) to afford the title compound (0.083 g, 9%) as white solid. Rf=0.47 (SiO2, CH2Cl2/AcOEt 1:1); Rf=0.39 (C18, 7:3 H2O/CH3CN). MS (ESI) m/z: 333 [M−H]+. FTIR (cm−1): 3414, 3222, 3050, 2965, 2929, 2871, 1825, 1720, 1612, 1550, 1449, 1262, 1232, 1119, 1068, 1031, 837, 711. 1H-NMR (CDCl3): δ 1.47 (d, 3H); 1.58-2.04 (m, 4H); 3.30-4.08 (m, 4H); 4.86-4.90 (m, 1H); 4.93-4.97 (m, 1H); 5.45 (t, 1H); 5.56 (br s, 1H); 7.39-7.44 (m, 5H).

Workup

  1. custom16 h
  2. customat rt
  3. customThe solvent was removed under vacuum
  4. customthe resulting crude mixture was purified by column chromatography
  5. washeluting with CH2Cl2/AcOEt (50:50)
  6. washeluting with H2O/CH3CN (70:30)

Sources & evidence

ORD record
ord-11213e0b2ddd438a9f5d3dd1a1c9ba2b
Source dataset
uspto-grants-2016_05
Patent number
US09353075B2

Reaction notes

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