tert-Butyl methyl ether → 1-benzylazetidine-2-carboxylic acid

HRID 2187335Notes

Reaction equation

C[O:2][C:3]([CH:5]1[CH2:8][CH2:7][N:6]1[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:4].COC(C)(C)C>O>[CH2:9]([N:6]1[CH2:7][CH2:8][CH:5]1[C:3]([OH:4])=[O:2])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 40 °C

Procedure

21.02 g of N-Benzylazetidine-2-carboxylic acid methyl ester, 592 g of t-butyl methyl ether and 40 g of water are mixed at 20 to 25° C. and then 1.41 g of enzyme (Chirazyme L-2) was added thereto and the resulting solution was heated to 40° C. and stirred for 14 hours. Settled solution was separated into an aqueous phase and an organic phase. The aqueous phase was washed twice with t-butyl methyl ether to yield an aqueous solution of optically active N-benzylazetidine-2-carboxylic acid and a combined organic phase of N-benzylazetidine-2-carboxylic acid methyl ester. Results of the same analysis as in the Example 1 is shown in Table 7.

Workup

addition1.41 g of enzyme (Chirazyme L-2) was added
customSettled solution was separated into an aqueous phase
washThe aqueous phase was washed twice with t-butyl methyl ether

Sources & evidence

ORD record: ord-2ea50708c8234d9d862bc4dea3daf171
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06410279B1

Reaction notes

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