Trifluoroacetic acid → HCID 12969041, compound

HRID 413728Notes

Reaction equation

HRID 413728 reaction equation
[CH2:1]([O:8][C:9]1[CH:43]=[CH:42][C:12]([O:13][CH2:14][C@@H:15]([OH:41])[CH2:16][N:17]([CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([NH:33][CH:34]3[S:38][C:37](=[O:39])[NH:36][C:35]3=[O:40])=[CH:29][CH:28]=2)C(=O)OC(C)(C)C)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:13][CH2:14][C@@H:15]([OH:41])[CH2:16][NH:17][CH2:25][CH2:26][C:27]2[CH:28]=[CH:29][C:30]([NH:33][CH:34]3[S:38][C:37](=[O:39])[NH:36][C:35]3=[O:40])=[CH:31][CH:32]=2)=[CH:42][CH:43]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86584667HCID 86584667, compound

Product 1

HCID 12969041HCID 12969041, compoundYield 58%

Procedure

This compound was prepared from tert-butyl (2S)-3-[4-(benzyloxy)phenoxy]-2-hydroxypropyl{4-[(2,4-dioxo-1,3-thiazolidin-5-yl)amino]phenethyl}carbamate and trifluoroacetic acid in substantially the same manner as described in example 1, step e, with one modification, the product was isolated as the free base and recrystallized from methanol, tetrahydrofuran, hexanes to give a yellow foam solid (58% yield): mp 152° C.; MS m/e 508 (M+H)+; 1H NMR (DMSO-d6 300 MHz) δ2.68 (m, 2H), 2.81 (m, 1H), 2.88 (m, 4H), 3.85 (m, 2H), 4.00 (m, 1H), 5.02 (s, 2H), 5.45 (br, 1H), 5.99 (d, 1H), 6.59 (d, 2H), 6.66 (d, 1H), 6.84 (d, 2H), 6.86 (m, 2H) 6.92 (m, 2H), 7.28 (m, 5H), 8.80 (br, 1 H);

Workup

  1. customthe product was isolated as the free base
  2. customrecrystallized from methanol, tetrahydrofuran, hexanes

Sources & evidence

ORD record
ord-73be69e358544b269c0ed953a20e93bc
Source dataset
uspto-grants-2003_05
Patent number
US06569873B2

Reaction notes

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