HCID 178451173, compound → HCID 69895915, compound

HRID 1871725Notes

Reaction equation

HRID 1871725 reaction equation
C([O:5][C:6]([C@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13](=[O:44])[CH2:14][O:15][C:16]1[CH:21]=[C:20]([C:22]2[NH:26][C:25](=[S:27])[O:24][N:23]=2)[CH:19]=[C:18]([O:28][CH2:29][C:30]([N:32]2[CH2:36][CH2:35][CH2:34][C@@H:33]2[C:37]([O:39]C(C)(C)C)=[O:38])=[O:31])[CH:17]=1)=[O:7])(C)(C)C>FC(F)(F)C(O)=O>[C:6]([C@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13](=[O:44])[CH2:14][O:15][C:16]1[CH:17]=[C:18]([CH:19]=[C:20]([C:22]2[N:26]=[C:25]([S:27][C:20]([CH3:22])([CH3:21])[CH3:19])[O:24][N:23]=2)[CH:21]=1)[O:28][CH2:29][C:30]([N:32]1[CH2:36][CH2:35][CH2:34][C@@H:33]1[C:37]([OH:39])=[O:38])=[O:31])([OH:5])=[O:7]

Participants

3

Reactant 1

HCID 178451173HCID 178451173, compound

Product 1

HCID 69895915HCID 69895915, compoundYield 111%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 315 mg (0.5 mmol) (R)-1-[[3-[2-[(R)-2-tert-butoxycarbonyl -pyrrolidin-1-yl]-2-oxo-ethoxy]-5-(5-thioxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl) -phenoxy]-acetyl]-pyrrolidine-2-carboxylic acid tert-butyl ester in 1.5 ml trifluoroacetic acid was stirred for 4 h at room temperature. The solvent was removed in vacuo and the residue suspended in 10 ml ether. The resulting suspension was stirred overnight. Filtration and drying gave 160 mg (57%) of the title compound as a white powder. MS m/e (%): 599 (M+Na+, 54), 594 (M+NH4+, 71), 577 (M+H+, 100), 521 (37).

Workup

  1. customThe solvent was removed in vacuo
  2. filtrationFiltration
  3. customdrying

Sources & evidence

ORD record
ord-75b8078a46c14781a9b94ec26d2fa100
Source dataset
uspto-grants-2000_08
Patent number
US06103910

Reaction notes

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