Pivaloyl chloride → HCID 12074006, compound

HRID 1368867Notes

Reaction equation

HRID 1368867 reaction equation
[CH3:1][O:2][P:3]([C@@H:6]([NH:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[CH3:7])(=O)[OH:4].C(Cl)(=O)C(C)(C)C.[OH:26][C@@H:27]([CH2:32][CH2:33][CH2:34][CH2:35][NH:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C:28]([O:30][CH3:31])=[O:29].NCCCCC(O)C(O)=O>O1CCCC1.C(N(CC)CC)C>[CH2:12]([O:11][C:9]([NH:8][C@H:6]([P:3]([O:2][CH3:1])([O:26][C@@H:27]([CH2:32][CH2:33][CH2:34][CH2:35][NH:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C:28]([O:30][CH3:31])=[O:29])=[O:4])[CH3:7])=[O:10])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 62493Pivaloyl chlorideHCID 517029HCID 517029, compoundHCID 12074004HCID 12074004, compoundHCID 12074005HCID 12074005, compound

Product 1

HCID 12074006HCID 12074006, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Procedure

(R)-1-(benzyloxycarbonylamino)ethylphophonic acid monomethyl ester (40.7 mg) described in Biochemistry, 6294(1989) was dissolved in tetrahydrofuran (1 ml), and pivaloyl chloride (71.8 mg) and triethylamine (90.4 mg) were added. The mixture was stirred at room temperature for 30 minutes, then added with a tetrahydrofuran (1 ml) solution of methyl (S)-2-hydroxy-6-(tert-butoxycarbonylamino)hexanoate (38.9 mg), which is obtainable from 6-amino-2-hydroxyhexanoic acid described in Chem. Pharm. Bull., 621(1976) by a conventional method, and stirred at room temperature overnight. The organic substances were extracted with ethyl acetate and the extract was washed with saturated brine, and then the organic layer was dried over anhydrous sodium sulfate. The residue was purified by silica gel thin-layer chromatography to obtain methyl (S)-2-(((R)-1-(benzyloxycarbonylamino)ethyl)(methoxyphosphinoyl)oxy)-6-(tert-butoxycarbonylamino)hexanoate (9.7 mg, 13%). This compound was subjected to the measurement of molecular weight and then used in the following reaction.

Workup

  1. stirring, 621(1976) by a conventional method, and stirred at room temperature overnight
  2. extractionThe organic substances were extracted with ethyl acetate
  3. washthe extract was washed with saturated brine
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. customThe residue was purified by silica gel thin-layer chromatography

Sources & evidence

ORD record
ord-a51040e6a0394b1f809a56e0946620d5
Source dataset
uspto-grants-2003_06
Patent number
US06576627B1

Reaction notes

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