Trifluoroacetic acid → HCID 178457430, compound

HRID 1603994Notes

Reaction equation

HRID 1603994 reaction equation
C([O:14][C:15]([C:17]1[O:18][C@@H:19]([C:45](=[O:51])[N:46]([CH3:50])[CH2:47][CH2:48][CH3:49])[C@H:20]([NH:41][C:42](=[O:44])[CH3:43])[C@@H:21]([NH:23][C:24]([NH:33]C(OC(C)(C)C)=O)=[N:25]C(OC(C)(C)C)=O)[CH:22]=1)=[O:16])(C1C=CC=CC=1)C1C=CC=CC=1.[F:52][C:53]([F:58])([F:57])[C:54]([OH:56])=[O:55]>ClCCl>[F:52][C:53]([F:58])([F:57])[C:54]([OH:56])=[O:55].[C:42]([NH:41][C@H:20]1[C@H:19]([C:45](=[O:51])[N:46]([CH3:50])[CH2:47][CH2:48][CH3:49])[O:18][C:17]([C:15]([OH:16])=[O:14])=[CH:22][C@@H:21]1[NH:23][C:24]([NH2:33])=[NH:25])(=[O:44])[CH3:43]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178457429HCID 178457429, compound

Product 1

HCID 178457430HCID 178457430, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(4S,5R,6R)-5-Acetylamino-4-[2,3-bis(tert-butoxycarbonyl)-guanidino]-6-(methylpropylcarbamoyl)-5,6-dihydro-4H-pyran-2-carboxylic acid benzhydryl ester (0.11 g) was dissolved in dichloromethane (1 ml) and trifluoroacetic acid (1 ml) and left to stand for 3 hours. The solvent was removed in vacuo and the residue was triturated using diethyl ether. The solid was collected by filtration and dried to give the title compound as a white solid. (0.061 g) 1H NMR (250 MHz, D2O) 6.00 (1H, d, J=4Hz), 5.34 (1H, d, J=6.3Hz), 4.43-4.29 (2H, m) 3.56-3.13 (2H, m), 3.13,2.93 (3H, 2xs), 2.00 (3H, s), 1.79-1.44 (2H, m), 0.88 (3H, m); Mass analysis:C16H24F3N5O7. Required C, 42.20; H, 5.31; N15.38. Found C, 42.24; H, 5.45; N, 15.09; Mass Spec (Low resolution):MH+ =342.

Workup

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

Sources & evidence

ORD record
ord-037229efc2ef4e989448f57d88a7dee4
Source dataset
uspto-grants-1999_11
Patent number
US05990156

Reaction notes

Loading…