Trifluoroacetic acid → HCID 70200487, compound

HRID 1603993Notes

Reaction equation

HRID 1603993 reaction equation
C([O:14][C:15]([C:17]1[O:18][C@@H:19]([C:35](=[O:41])[N:36]([CH3:40])[CH2:37][CH2:38][CH3:39])[C@H:20]([NH:31][C:32](=[O:34])[CH3:33])[C@@H:21]([NH:23]C(OC(C)(C)C)=O)[CH:22]=1)=[O:16])(C1C=CC=CC=1)C1C=CC=CC=1.[F:42][C:43]([F:48])([F:47])[C:44]([OH:46])=[O:45]>ClCCl>[F:42][C:43]([F:48])([F:47])[C:44]([OH:46])=[O:45].[C:32]([NH:31][C@H:20]1[C@H:19]([C:35](=[O:41])[N:36]([CH3:40])[CH2:37][CH2:38][CH3:39])[O:18][C:17]([C:15]([OH:16])=[O:14])=[CH:22][C@@H:21]1[NH2:23])(=[O:34])[CH3:33]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10603036HCID 10603036, compound

Product 1

HCID 70200487HCID 70200487, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(4S,5R,6R)-5-Acetylamino-4-(tert-butoxycarbonylamino)-6-(methyl-propylcarbamoyl)-5,6-dihydro-4H-pyran-2-carboxylic acid benzhydryl ester (0.10 g) was dissolved in dichloromethane (1 ml) and trifluoroacetic acid (1 ml) and left to stand at 23° C. for 3 hours. The solvent was removed in vacuo and the residue was triturated using diethyl ether (30 ml). The resulting solid was collected by filtration and dried to give the title compound as a white solid. (0.064 g): 1H NMR (250MHz, D2O) 5.99 (1H, m), 5.24 (1H, m), 4.52 (1H, m), 4.25 (1H, m), 3.59-3.18 (2H, m), 3.18+2.97 (3H, s), 2.02 (3H, s), 1.72-1.46 (2H, m), 0.87 (3H, m); Mass Analysis: C15H22F3N3O7. 0.25H2O. Required C, 43.12; H, 5.43; N, 10.06; Found C, 42.99; H, 5.60; N, 10.17; Mass Spec. (Low Resolution) MH+ =300.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was triturated
  3. filtrationThe resulting solid was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-b88d7513851e45339fc0e8b8b62547aa
Source dataset
uspto-grants-1999_11
Patent number
US05990156

Reaction notes

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