Trifluoroacetic acid → HCID 86695475, compound

HRID 1487527Notes

Reaction equation

HRID 1487527 reaction equation
C(OC(=O)[N:7]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([C@@H:26]([OH:36])[C@H:27]([NH:30][C:31](=[O:35])[CH:32]([Cl:34])[Cl:33])[CH2:28][F:29])=[CH:22][CH:21]=2)=[CH:16][N:15]=1)[CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:34][CH:32]([Cl:33])[C:31]([NH:30][C@H:27]([CH2:28][F:29])[C@H:26]([OH:36])[C:23]1[CH:22]=[CH:21][C:20]([C:17]2[CH:16]=[N:15][C:14]([CH2:13][NH:7][CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])=[CH:19][CH:18]=2)=[CH:25][CH:24]=1)=[O:35]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86695476HCID 86695476, compound

Product 1

HCID 86695475HCID 86695475, compoundYield 125.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (5-{4-[(1R,2S)-2-(2,2-Dichloro-acetylamino)-3-fluoro-1-hydroxy-propyl]-phenyl}-pyridin-2-ylmethyl)-(3-methyl-butyl)-carbamic acid tert-butyl ester (8 mg, 0.014 mmol) in dry CH2Cl2 (0.04 mL) is added trifluoroacetic acid (0.04 mL) and resulting reaction mixture is stirred at room temperature for 2 hours. Solvent is evaporated in vacuo to get brown crude, which is washed with diethyl ether:pentane (1:9), to give the title compound (8 mg): 1H-NMR (400 MHz, DMSO-d6) δ0.89 (d, 6H, J=6.40 Hz), 1.52-1.58 (m, 2H), 1.60-1.65 (m, 1H), 3.01 (bs, 1H), 4.20-4.23 (m, 2H), 4.29-4.31 (m, 0.5H), 4.36-4.38 (m, 2H), 4.40-4.44 (m, 0.5H), 4.57-4.59 (m, 0.5H), 4.70-4.71 (m, 0.5H), 4.91-4.93 (m, 1H), 6.02 (d, 1H, J=4.28 Hz), 6.52 (s, 1H), 7.49 (d, 2H, J=8.24), 7.57 (d, 1H, J=8.16 Hz), 7.73 (d, 2H, J=8.28 Hz), 8.19 (dd, 1H, J1=8.16 Hz, J2=2.32 Hz), 8.65 (d, 1H, J=8.96 Hz), 8.96 (d, 1H, J=1.96 Hz), 9.00 (bs, 2H). LC-MS (m/z): [M+H]=456.1.

Workup

  1. customresulting
  2. customreaction mixture
  3. customSolvent is evaporated in vacuo
  4. customto get brown crude, which
  5. washis washed with diethyl ether:pentane (1:9)

Sources & evidence

ORD record
ord-c8b86a9f2132441d86544eb9b45cf9f7
Source dataset
uspto-grants-2016_08
Patent number
US09428528B2

Reaction notes

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