Water → HCID 71722586, compound

HRID 882389Notes

Reaction equation

HRID 882389 reaction equation
[Cl:1][C:2]1[C:3]([F:65])=[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:62]=[CH:61][C:34]([C:35]([O:37][CH:38]([O:40][C:41]([O:43][C@@H:44]3[C@H:48]4[O:49]C(C)(C)[O:51][C@H:47]4[O:46][C@@H:45]3[C@H:54]3[CH2:58][O:57]C(C)(C)[O:55]3)=[O:42])[CH3:39])=[O:36])=[CH:33][C:32]=2[O:63][CH3:64])=[O:29])[CH:5]=[CH:6][CH:7]=1.FC(F)(F)C(O)=O.O>>[OH:55][C@@H:54]([C@@H:45]1[C@H:44]([O:43][C:41]([O:40][CH:38]([O:37][C:35](=[O:36])[C:34]2[CH:61]=[CH:62][C:31]([NH:30][C:28]([C@H:9]3[C@H:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=4[F:65])[C@:12]([C:15]4[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=4[F:22])([C:13]#[N:14])[C@H:11]([CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])[NH:10]3)=[O:29])=[C:32]([O:63][CH3:64])[CH:33]=2)[CH3:39])=[O:42])[C@@H:48]([OH:49])[C@@H:47]([OH:51])[O:46]1)[CH2:58][OH:57]

Participants

4

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 86696315HCID 86696315, compound

Product 1

HCID 71722586HCID 71722586, compound

Procedure

In a 15 mL round-bottomed flask was charged with 1-(((3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,2-d][1,3]dioxol-6-yloxy)carbonyloxy)ethyl 4-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)-3-methoxybenzoate (111 mg, 117 μmol). The mix of trifluoroacetic acid (1.48 g, 1 mL, 13.0 mmol) and water (375 mg, 375 μl, 20.8 mmol) was added. LC-MS indicated the completion of the reaction after stirring at room temperature for 1 h.

Workup

  1. additionwas added
  2. customthe completion of the reaction

Sources & evidence

ORD record
ord-f8ede3e20c64437ba64fc5ec26dd60a5
Source dataset
uspto-grants-2015_03
Patent number
US08993614B2

Reaction notes

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