Water → HCID 131712762, compound

HRID 1156809Notes

Reaction equation

HRID 1156809 reaction equation
C([O:3][P:4]([CH2:16][C:17]([N:19]1[CH2:34][C@@H:33]([S:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:32][C@H:20]1[C:21]([O:23][CH2:24][O:25][C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28])=[O:22])=[O:18])([CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:5])C.Br[Si](C)(C)C.O.C(=O)(O)[O-].[Na+]>ClCCl>[OH:5][P:4]([CH2:16][C:17]([N:19]1[CH2:34][C@@H:33]([S:35][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH2:32][C@H:20]1[C:21]([O:23][CH2:24][O:25][C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28])=[O:22])=[O:18])([CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:3]

Participants

6

Reactant 4

HCID 962Water2×HCID 76113BromotrimethylsilaneHCID 516892Sodium BicarbonateHCID 13136850HCID 13136850, compound

Product 1

HCID 131712762HCID 131712762, compoundYield 62.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (cis)-1-[[ethoxy(4-phenylbutyl)phosphinyl]-acetyl]-4-(phenylthio)-L-proline, (2,2-dimethyl-1-oxopropoxy)methyl ester (3 g) in dichloromethane (30 ml) is added bromotrimethylsilane (1.2 g). The mixture is stirred at room temperature for 16 hours. After the addition of water (15 ml), saturated sodium bicarbonate (25 ml) is added, followed by water (500 ml) to effect solution. The aqueous alkaline solution is washed with ether and acidified to a pH of 3 with concentrated hydrochloric acid. The oil that separates from solution is extracted into ethyl acetate, washed with brine, and dried (MgSO4). The solvent is removed in vacuo to give a residue of 2.5 g which is chromatographed on silica gel (120 g) eluting with dichloromethane/methanol/acetic acid (19:1:1) to give the product (1.8 g) as a glass-like solid.

Workup

  1. additionis added
  2. washThe aqueous alkaline solution is washed with ether
  3. extractionThe oil that separates from solution is extracted into ethyl acetate
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. customThe solvent is removed in vacuo
  7. customto give a residue of 2.5 g which
  8. customis chromatographed on silica gel (120 g)
  9. washeluting with dichloromethane/methanol/acetic acid (19:1:1)

Sources & evidence

ORD record
ord-d1e2f3e87c004a7584ca82da71f9fc47
Source dataset
uspto-grants-1982_06
Patent number
US04337201

Reaction notes

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