Lithium Hydroxide → 1-Phenylmethanesulfonyl-azetidine-2-carboxylic acid

HRID 7906Notes

Reaction equation

C[O:2][C:3]([CH:5]1[CH2:8][CH2:7][N:6]1[S:9]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:11])=[O:10])=[O:4].[OH-].[Li+]>CO>[C:13]1([CH2:12][S:9]([N:6]2[CH2:7][CH2:8][CH:5]2[C:3]([OH:4])=[O:2])(=[O:11])=[O:10])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 0 °C

Procedure

1-Phenylmethanesulfonyl-azetidine-2-carboxylic acid methyl ester (1.13 g, 4.19 mmoles) was dissolved in methanol (20 mL) and cooled to 0° C. Treatment of this solution with aqueous lithium hydroxide (7.75 mL, 1 M) was followed by warming to ambient temperature over a 3 hour period. Most of the methanol was removed in vacuo and the pH was adjusted to 1 by treatment with 1 M HCl. The product was extracted into ethyl acetate, dried over anhydrous sodium sulfate and concentrated to afford 886 g (83%) of the product as a white solid. 1H NMR (CDCl3) δ2.37–2.57 (m, 2H); 3.21–3.31 (m, 1H); 3.81 (s, 3H); 4.01 (q, 1H, J=8.6); 4.33 (d, 1H, J=13.7); 4.44 (d, 1 H, J=13.7); 4.98 (dd, 1H, 9.4, 8.6); 7.34–7.53 (series of m, 5H).

Workup

temperatureby warming to ambient temperature over a 3 hour period
customMost of the methanol was removed in vacuo
extractionThe product was extracted into ethyl acetate
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-7d8656799d6241dcb7cc7ca2a9e1f1af
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07087628B2

Reaction notes

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