Water → F2147-0175

HRID 1990690Notes

Reaction equation

HRID 1990690 reaction equation
COC(C)(C)C.[CH2:7]([O:9][C:10](=[O:23])[CH2:11][N:12]([CH2:20][C:21]#[CH:22])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH3:8].P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>C(#N)C>[C:16]([O:15][C:13]([N:12]([CH2:20][C:21]#[CH:22])[CH2:11][C:10]([OH:23])=[O:9])=[O:14])([CH3:19])([CH3:18])[CH3:17].[CH2:7]([O:9][C:10](=[O:23])[CH2:11][N:12]([CH2:20][C:21]#[CH:22])[C:13]([O:15][C:16]([CH3:18])([CH3:19])[CH3:17])=[O:14])[CH3:8]

Participants

7

Reactant 4

HCID 962WaterHCID 15413tert-Butyl methyl etherHCID 62657Potassium Phosphate, TribasicHCID 87489340HCID 87489340, compound

Product 2

HCID 10262630F2147-0175HCID 87489340HCID 87489340, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Various enzymes shown in the following Table 1 were weighed in amounts shown in the following Table 2, respectively. Then, into the above-mentioned enzyme was added a solution prepared by dissolving 0.1 ml of a 2 M tert-butyl methyl ether solution of N-tert-butoxycarbonyl-propargylglycine ethyl ester into 5 ml of a 100 mM potassium phosphate buffering solution (pH 7.0). The resultant solution was stirred at 40° C. for 20 hours. Then, 6.4 ml of water and 8.6 ml of acetonitrile were added and mixed. The resultant uniform solution was analyzed by HPLC [column: CHIRALCEL OJ-RH, 4.6 mmφ×15 cm (manufactured by Daicel Chemical Industries, Ltd.)], and the yields and enantiomer excess of the resultant optically active N-tert-butoxycarbonyl-propargylglycine and N-tert-butoxycarbonyl-propargylglycine ethyl ester were calculated. The results are shown in Table 2.

Workup

  1. additionThen, into the above-mentioned enzyme was added a solution
  2. customprepared
  3. additionmixed

Sources & evidence

ORD record
ord-dc0249cd8718417b8dfdd924101ff8c2
Source dataset
uspto-grants-2010_01
Patent number
US07645607B2

Reaction notes

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