Bromotrimethylsilane → HCID 131713507, compound

HRID 544100Notes

Reaction equation

HRID 544100 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-9439025163e9482d84f66aaf7c7d8d40
Source dataset
uspto-grants-1984_05
Patent number
US04448772

Reaction notes

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