Hydrochloric Acid → HCID 131714424, compound

HRID 652356Notes

Reaction equation

HRID 652356 reaction equation
C(OC([N:8]1[C@@H:12]([CH2:13][CH:14]([CH3:16])[CH3:15])[CH:11]([CH2:17][N:18]([C:35]([O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[O:36])[C@H:19]([C:24]([NH:26][C@H:27]([C:31]([O:33][CH3:34])=[O:32])[CH:28]([CH3:30])[CH3:29])=[O:25])[CH2:20][CH:21]([CH3:23])[CH3:22])[O:10]C1(C)C)=O)(C)(C)C.FC(F)(F)C(O)=O.Cl.C(=O)(O)[O-].[Na+]>ClCCl>[NH2:8][C@@H:12]([CH2:13][CH:14]([CH3:16])[CH3:15])[CH:11]([OH:10])[CH2:17][N:18]([C:35]([O:37][CH2:38][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)=[O:36])[C@H:19]([C:24]([NH:26][C@H:27]([C:31]([O:33][CH3:34])=[O:32])[CH:28]([CH3:30])[CH3:29])=[O:25])[CH2:20][CH:21]([CH3:22])[CH3:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 131714425HCID 131714425, compound

Product 1

HCID 131714424HCID 131714424, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 177 mg (nom. 0.27 mmol) of N-[N-[[(4S)-3-[(t-butyloxy)carbonyl]-2,2-dimethyl-4-(2-methylpropyl)-5-oxazolidinyl]methyl]-N-[(phenylmethoxy)carbonyl]-L-leucyl]-L-valine, methyl ester (Isomer A) in 1.7 ml of dry dichloromethane was cooled in an ice bath under nitrogen, then treated with 0.85 ml of distilled trifluoroacetic acid. After 11/2 hours, the reaction was concentrated in vacuo to an oil, dissolved in 1 ml of distilled tetrahydrofuran, and treated with 0.6 ml (0.6 mmol) of 1N hydrochloric acid. After four hours, the reaction was worked up by treating with 6 ml of saturated sodium bicarbonate (aqueous), then extracting with 2×6 ml of chloroform, washing the organic extracts with brine, drying (magnesium sulfate), and concentrating to afford 127 mg of the title compound as a crude oil.

Workup

  1. concentrationAfter 11/2 hours, the reaction was concentrated in vacuo to an oil
  2. dissolutiondissolved in 1 ml of distilled tetrahydrofuran
  3. extractionextracting with 2×6 ml of chloroform
  4. washwashing the organic extracts with brine
  5. dry with materialdrying (magnesium sulfate)
  6. concentrationconcentrating

Sources & evidence

ORD record
ord-996b6e632b63431092afe13be6538e6d
Source dataset
uspto-grants-1987_06
Patent number
US04670541

Reaction notes

Loading…