Trifluoroacetic acid → HCID 86663947, compound

HRID 576881Notes

Reaction equation

HRID 576881 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C@H:16]([N:27]([C:30](OC(C)(C)C)=O)[NH:28]C)[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C@H:16]([N:27]([CH3:30])[NH2:28])[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86663948HCID 86663948, compound

Product 1

HCID 86663947HCID 86663947, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-benzyl 3-(4-(benzyloxy)phenyl)-2-(N-(tert-butoxycarbonyl)-N′-methylhydrazinyl)propanoate (Compound XXVII-1) 491 mg (1.00 mmol) in dichloromethane 1 ml, trifluoroacetic acid 743 μl (10.0 mmol) was added and the mixture was stirred at room temperature for 0.5 hr. The reaction mixture was concentrated in vacuo and the residue was diluted with ethyl acetate 50 ml and washed with saturated sodium bicarbonate solution 50 ml. The organic phase was washed with water 50 ml and brine 50 ml. The organic phase was dried over magnesium sulfate and filtered. The mother solution was concentrated in vacuo to give the title compound, which was used without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe residue was diluted with ethyl acetate 50 ml
  3. washwashed with saturated sodium bicarbonate solution 50 ml
  4. washThe organic phase was washed with water 50 ml and brine 50 ml
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe mother solution was concentrated in vacuo

Sources & evidence

ORD record
ord-7bf5a12b64a94993adf3b7a42c190367
Source dataset
uspto-grants-2015_05
Patent number
US09040531B2

Reaction notes

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