Hydrazine hydrate (1:1) → HCID 178443706, compound

HRID 2357075Notes

Reaction equation

HRID 2357075 reaction equation
CC1(C)[N:6](C(OC(C)(C)C)=O)[C@:5]([CH3:38])([C:14](=O)[CH2:15][C:16]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[C:20]([C:33]([F:36])([F:35])[F:34])[CH:19]=2)=O)[CH2:4][O:3]1.O.[NH2:41][NH2:42].C(O)(C(F)(F)F)=O.C(Cl)Cl>CO>[NH2:6][C@@:5]([C:14]1[CH:15]=[C:16]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[C:20]([C:33]([F:36])([F:35])[F:34])[CH:19]=2)[NH:42][N:41]=1)([CH3:38])[CH2:4][OH:3]

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 21863450Trifluoroacetic acid methylene chlorideHCID 68455964HCID 68455964, compound

Product 1

HCID 178443706HCID 178443706, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The solution of (S)-tert-butyl 2,2,4-trimethyl-4-(3-(4-(octyloxy)-3-(trifluoromethyl)-phenyl)-3-oxo-propanoyl)oxazolidine-3-carboxylate (27 mg, 0.05 mmol, 1.0 equiv) and hydrazine monohydrate (2.7 μL, 0.055 mmol, 1.1 equiv) in methanol (0.2 mL) was stirred at room temperature for 2 hours. The reaction was condensed and the residue was treated with 20% TFA-DCM for 30 min. After removal of excess amount of TFA and DCM, the crude product was purified by prep. HPLC and afforded the title compound as mono-TFA salt (5.0 mg). MS (ESI, M+H+)=414.0; 1H NMR (400 MHz, CD3OD) δ 7.81 (s, 1H), 7.76 (d, 1H, J=9.2 Hz), 7.14 (d, 1H, J=9.2 Hz), 6.56 (s, 1H), 4.03 (t, 2H, J=6.0 Hz), 3.79, 3.67 (AB, 2H, J=12.0 Hz), 1.76-1.69 (m, 2H), 1.59 (s, 3H), 1.46-1.38 (m, 2H), 1.32-1.16 (m, 8H), 0.81 (t, 3H, J=7.2 Hz).

Workup

  1. customcondensed
  2. customAfter removal of excess amount of TFA and DCM
  3. customthe crude product was purified by prep

Sources & evidence

ORD record
ord-d32f3131a74347e9bd0cc533ddc1345d
Source dataset
uspto-grants-2010_07
Patent number
US07759370B2

Reaction notes

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