Trifluoroacetic acid → HCID 86589155, compound

HRID 1062892Notes

Reaction equation

HRID 1062892 reaction equation
C(OC([NH:8][C@H:9]([C:11]([NH:13][C@H:14]([C:18]([NH:20][CH2:21][CH:22]([CH3:24])[CH3:23])=[O:19])[CH:15]([CH3:17])[CH3:16])=[O:12])[CH3:10])=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:8][C@H:9]([C:11]([NH:13][C@H:14]([C:18]([NH:20][CH2:21][CH:22]([CH3:24])[CH3:23])=[O:19])[CH:15]([CH3:16])[CH3:17])=[O:12])[CH3:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86589156HCID 86589156, compound

Product 1

HCID 86589155HCID 86589155, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(tert-butoxycarbonyl)-L-alanyl-N1-isobutyl-L-valinamide (247 mg, 0.72 mmol) is stirred for 30 min under nitrogen with 1 mL of trifluoroacetic acid and 3 mL of dichloromethane. It is concentrated on a rotary evaporator. To the residue is added 2 mL of saturated sodium bicarbonate (pH=8). The product is diluted with 100 mL of ethyl ether. The aqueous salt is siphoned out and anhydrous sodium sulfate is added. The solution is filtered through glass wool and concentrated to 136 mg of the title compound as an off-white solid. NMR (MeOD)-d3 δ 4.66 (bs) 4.16 (d, J=8 Hz, 1H), 4.00 (q, J=7 Hz, 1H), 3.07 (dd, 1H), 2.98 (dd, 1H), 2.05 (m, 1H), 1.79 (m, 1H), 1.49 (d, J=7 Hz, 3H), 0.99 (d, J=7 Hz, 6H) 0.93 (d, J=7 Hz, 6H). HRMS (ESI) calcd for C12H25N3O2+H1 244.2025, found 244.2023.

Workup

  1. concentrationIt is concentrated on a rotary evaporator
  2. additionTo the residue is added 2 mL of saturated sodium bicarbonate (pH=8)
  3. additionThe product is diluted with 100 mL of ethyl ether
  4. additionanhydrous sodium sulfate is added
  5. filtrationThe solution is filtered through glass wool
  6. concentrationconcentrated to 136 mg of the title compound as an off-white solid

Sources & evidence

ORD record
ord-17b1ab606f6b476498918a2b5467538f
Source dataset
uspto-grants-2005_11
Patent number
US06962934B2

Reaction notes

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