Trifluoroacetic acid → HCID 68516234, compound

HRID 1716316Notes

Reaction equation

HRID 1716316 reaction equation
C([O:5][N:6]1[CH2:12][CH2:11][CH2:10][N:9]([CH3:13])[C@@H:8]([CH2:14][N:15]([S:33]([CH3:36])(=[O:35])=[O:34])[C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=3)=[CH:18][CH:17]=2)[C:7]1=[O:37])(C)(C)C.FC(F)(F)C(O)=O.CCCCCC>CCOCC>[OH:5][N:6]1[CH2:12][CH2:11][CH2:10][N:9]([CH3:13])[C@@H:8]([CH2:14][N:15]([S:33]([CH3:36])(=[O:35])=[O:34])[C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=3)=[CH:18][CH:17]=2)[C:7]1=[O:37]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8058HexaneHCID 68513933HCID 68513933, compound

Product 1

HCID 68516234HCID 68516234, compoundYield 104.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of (3S)-1-t-butoxy-3-{N-methanesulfonyl-N-[4-(4-trifluoromethyl-phenoxy)phenyl]amino}methyl-4-methyl-1,4-diazepan-2-one (146 mg, 0.2 mmol) from Step G in Et2O (0.5 mL) at room temperature was added trifluoroacetic acid (1.5 mL) slowly. The mixture was stirred for 1 h at rt. The mixture was poured into Et2O/pure H2O (10 mL/30 mL) and hexane (20 mL) was then added. The organic layer was extracted with pure H2O (30 mL). The aqueous layers were collected and combined. After lyophilization gave 102 mg of the titled compound (85%) as a white trifluoroacetic acid salt. 1H NMR (300 MHz, d6-DMSO) δ 10.05-10.00 (br s, 1H), 7.77 (d, J=9.0 Hz, 2H), 7.56 (d, J=9.0 Hz, 2H), 7.21 (d, J=9.0 Hz, 2H), 7.18 (d, J=9.0 Hz, 2H), 4.5-4.0 (m, 5H), 3.37-3.31 (m, 1H), 3.09-3.06 (m, 4H), 2.51 (br s, 3H), 2.14-1.84 (m, 2H); MS (EI) 510 (M++Na), 488 (M++1, 100).

Workup

  1. additionwas then added
  2. extractionThe organic layer was extracted with pure H2O (30 mL)
  3. customThe aqueous layers were collected

Sources & evidence

ORD record
ord-05944815df9b48dcbab01dea3e7c4975
Source dataset
uspto-grants-2010_09
Patent number
US07803793B2

Reaction notes

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