Phosphate → HCID 57235838, compound

HRID 65433Notes

Reaction equation

HRID 65433 reaction equation
N12CCCCC1C=NCCC2.[CH2:12]([N:19]([CH2:26][S:27]([C:30]([CH3:33])([CH3:32])[CH3:31])(=[O:29])=[O:28])[C:20](=[O:25])[C@@H:21](Br)[CH2:22][OH:23])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(Cl)Cl.P([O-])([O-])([O-])=O>O1CCCC1>[CH2:12]([N:19]([CH2:26][S:27]([C:30]([CH3:33])([CH3:32])[CH3:31])(=[O:29])=[O:28])[C:20](=[O:25])[C@@H:21]1[O:23][CH2:22]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 1061PhosphateHCID 6344DichloromethaneHCID 3141121,5-Diazabicyclo(5,4,0)undec-5-eneHCID 57204252HCID 57204252, compound

Product 1

HCID 57235838HCID 57235838, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.125 g (7.4 mmol) of 1,5-diazabicyclo[5.4.0]undec-5-ene are added at 0° to a solution of 118 g (3 mmol) of N-benzyl-N-tert.-butylsulphonylmethyl-2-(S)-bromo-3-hydroxypropionic acid amide (see Example 4) in 15 ml of absolute tetrahydrofuran and the whole is stirred for a further 90 minutes at room temperature. After working up with methylene chloride and phosphate buffer having a pH of 7.0, the crude product obtained from the organic phase is chromatographed over 50 g of silica gel. After eluting with a mixture of ethyl acetate/toluene (1:1), the pure title compound, identical to the compound according to Example 6, is obtained.

Sources & evidence

ORD record
ord-04e6a4c09d8f47e68a26886d780d845f
Source dataset
uspto-grants-1986_09
Patent number
US04614614

Reaction notes

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