Trifluoroacetic acid → HCID 71748116, compound

HRID 2277099Notes

Reaction equation

[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:8][C:9]1[CH:23]=[CH:22][C:12]([CH2:13][NH:14]C(=O)OC(C)(C)C)=[C:11]([CH2:24][NH:25][C:26]([C@@H:28]2[CH2:33][O:32][CH2:31][CH2:30][N:29]2[C:34](=[O:41])[C@H:35]([OH:40])[C:36]([CH3:39])([CH3:38])[CH3:37])=[O:27])[CH:10]=1>C(Cl)Cl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:14][CH2:13][C:12]1[CH:22]=[CH:23][C:9]([Cl:8])=[CH:10][C:11]=1[CH2:24][NH:25][C:26]([C@@H:28]1[CH2:33][O:32][CH2:31][CH2:30][N:29]1[C:34](=[O:41])[C@H:35]([OH:40])[C:36]([CH3:39])([CH3:38])[CH3:37])=[O:27]

Participants

Conditions

Temperature: 0 °C

Procedure

Trifluoroacetic acid (50% solution in CH2Cl2, 3 mL) was added to a solution of tert-Butyl 4-chloro-2-[{(S)-4-{(R)-2-hydroxy-3,3-dimethylbutanoyl}morpholine-3-carboxamido}-methyl]-benzylcarbamate (0.25 g, 0.50 mmol) in CH2Cl2 (1 mL) and the reaction was stirred at 0° C. for 30 min. The reaction mixture was concentrated under reduced pressure and residue was triturated with diethyl ether to afford the title compound as a white hygroscopic solid. 1HNMR (400 MHz, CD3CN): 8.37 (t, J=4.0 Hz, 1H), 8.05 (bs, 3H), 7.46-7.43 (m, 2H), 7.34 (dd, J=8.4 Hz, J=2.4 Hz, 1H), 4.78 (d, J=4.0 Hz, 1H), 4.46 (dd, J=15.2, 6.0 Hz, 1H), 4.39-4.43 (m, 3H), 4.22 (d, J=2.8 Hz, 2H), 3.91 (d, J=12.4 Hz, 2H), 3.86 (dd, J=11.6, 2.4 Hz, 1H), 3.58 (dd, J=8.4 Hz, J=4.0 Hz, 1H), 3.53-3.42 (m, 2H), 0.98 (s, 9H).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure and residue
customwas triturated with diethyl ether

Sources & evidence

ORD record: ord-d4625f4e3b8c4524a6a9d39f7d58ce8c
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133147B2

Reaction notes

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