Trifluoroacetic acid → HCID 72201100, compound

HRID 2206390Notes

Reaction equation

[Cl:1][C:2]1[C:3]([F:57])=[C:4]([C@@H:8]2[C@:12]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[F:22])([C:13]#[N:14])[C@H:11]([CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])[NH:10][C@H:9]2[C:28]([NH:30][C:31]2[CH:54]=[CH:53][C:34]([C:35]([O:37][CH2:38][CH2:39][O:40][P:41]([O:48]C(C)(C)C)([O:43]C(C)(C)C)=[O:42])=[O:36])=[CH:33][C:32]=2[O:55][CH3:56])=[O:29])[CH:5]=[CH:6][CH:7]=1.[F:58][C:59]([F:64])([F:63])[C:60]([OH:62])=[O:61]>C(Cl)Cl>[F:58][C:59]([F:64])([F:63])[C:60]([OH:62])=[O:61].[Cl:1][C:2]1[C:3]([F:57])=[C:4]([C@@H:8]2[C@:12]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[F:22])([C:13]#[N:14])[C@H:11]([CH2:23][C:24]([CH3:25])([CH3:26])[CH3:27])[NH:10][C@H:9]2[C:28]([NH:30][C:31]2[CH:54]=[CH:53][C:34]([C:35]([O:37][CH2:38][CH2:39][O:40][P:41]([OH:48])([OH:43])=[O:42])=[O:36])=[CH:33][C:32]=2[O:55][CH3:56])=[O:29])[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of chiral 2-(di-tert-butoxyphosphoryloxy)ethyl 4-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)-3-methoxybenzoate (Example 12, 89.1 mg, 0.104 mmol) in methylene chloride (2 mL) was treated with trifluoroacetic acid (1 mL) and stirred for 45 min at 0° C. The reaction mixture was concentrated and the product was lyophilized to give chiral 2-(phosphonooxy)ethyl 4-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)-3-methoxybenzoate trifluoroacetate as a white solid (80.7 mg, 90% yield). MS (ES+) m/z calcd. for C33H35Cl2F2N3O8P: [(M+H)+]: 740. found: 740.

Workup

concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record: ord-2ca50640a7104b809d215d724ff116f5
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371280B2

Reaction notes

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