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

HRID 2187336Notes

Reaction equation

C([O:3][C:4]([CH:6]1[CH2:9][CH2:8][N:7]1[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:5])C.COC(C)(C)C>O>[CH2:10]([N:7]1[CH2:8][CH2:9][CH:6]1[C:4]([OH:5])=[O:3])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 40 °C

Procedure

10.0 g of N-Benzylazetidine-2-carboxylic acid ethyl ester, 29.6 g of t-butyl methyl ether and 26.7 g of water are mixed at 20 to 25° C. and then 0.333 g of Enzyme (Chirazyme L-2) was added thereto and the resulting solution was heated to 40° C. and stirred for 7 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 ethyl ester. Results of the same analysis as in the Example 1 is shown in Table 8.

Workup

addition0.333 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-9811c127de5f4578b5b966bcf374d2f9
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06410279B1

Reaction notes

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