Bromotrimethylsilane → HCID 11533563, compound

HRID 133819Notes

Reaction equation

HRID 133819 reaction equation
[CH3:1][NH:2][C@H:3]([C:13]([NH:15][C@H:16]([C:21]([N:23]([C@@H:25]([CH:37]([CH3:39])[CH3:38])/[CH:26]=[C:27](/[P:29]([O:34]CC)([O:31]CC)=[O:30])\[CH3:28])[CH3:24])=[O:22])[C:17]([CH3:20])([CH3:19])[CH3:18])=[O:14])[C:4]([CH3:12])([CH3:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C[Si](Br)(C)C>C(Cl)Cl>[CH3:1][NH:2][C@H:3]([C:13]([NH:15][C@H:16]([C:21]([N:23]([C@@H:25]([CH:37]([CH3:39])[CH3:38])/[CH:26]=[C:27](/[P:29]([OH:31])([OH:34])=[O:30])\[CH3:28])[CH3:24])=[O:22])[C:17]([CH3:20])([CH3:19])[CH3:18])=[O:14])[C:4]([CH3:11])([CH3:12])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 86596605HCID 86596605, compound

Product 1

HCID 11533563HCID 11533563, compoundYield 23.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N,β,β-trimethyl-L-phenylalanyl-N1-[(1S,2E)-3-(diethoxyphosphoryl)-1-isopropyl-but-2-enyl]-N1,3-dimethyl-L-valinamide (11 mg, 0.02 mmol, from Example 71) in CH2Cl2 (0.5 mL) is treated with TMSBr (23 mg, 0.15 mmol). The reaction mixture is stirred at room temperature for 20 h, then concentrated. The residue is purified by reversal phase HPLC (mobile phase A: 0.02% TFA/H2O, mobile phase B: 0.02% TFA/CH3CN) to give 2.4 mg (19%) of desired product as a white solid. HRMS (ESI) calcd for C26H44N3O5P [M+H] 510.3091, found 510.3086.

Workup

  1. concentrationconcentrated
  2. customThe residue is purified by reversal phase HPLC (mobile phase A: 0.02% TFA/H2O, mobile phase B: 0.02% TFA/CH3CN)

Sources & evidence

ORD record
ord-4338b06dd3444f7f9b4057be9c1880b9
Source dataset
uspto-grants-2008_06
Patent number
US07390910B2

Reaction notes

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