Bromotrimethylsilane → HCID 131713507, compound

HRID 638166Notes

Reaction equation

HRID 638166 reaction equation
[CH3:1][N:2]([CH2:20][P:21]([O:33]CC)([CH2:23][CH2:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:22])[C:3]([N:5]1[CH2:19][CH2:18][CH2:17][C@H:6]1[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])=[O:4].C[Si](Br)(C)C>ClCCl>[CH3:1][N:2]([CH2:20][P:21]([OH:33])([CH2:23][CH2:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:22])[C:3]([N:5]1[CH2:19][CH2:18][CH2:17][C@H:6]1[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])=[O:4]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 131713506HCID 131713506, compound

Product 1

HCID 131713507HCID 131713507, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-[[methyl[[ethoxy(4-phenylbutyl)phosphinyl]methyl]amino]carbonyl]-L-proline, phenylmethyl ester, dry dichloromethane, and trimethylsilylbromide is stirred under argon at room temperature for several hours. The dichloromethane and excess trimethylsilylbromide are removed in vacuo and the residue is partitioned between ethyl acetate/water. The organic phase is washed with brine, dried, and evaporated to give 1-[[methyl[[hydroxy(4-phenylbutyl)phosphinyl]methyl]amino]carbonyl]-L-proline, phenylmethyl ester.

Workup

  1. customThe dichloromethane and excess trimethylsilylbromide are removed in vacuo
  2. customthe residue is partitioned between ethyl acetate/water
  3. washThe organic phase is washed with brine
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-478ac4e2449f46b692362c42c9905f23
Source dataset
uspto-grants-1985_12
Patent number
US04560681

Reaction notes

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