Hydrochloric Acid → HCID 18337544, compound

HRID 1760798Notes

Reaction equation

C[O:2][C:3](=[O:36])[C@H:4]([N:11]([S:22]([C:25]1[C:30]([CH3:31])=[CH:29][C:28]([O:32][CH3:33])=[C:27]([CH3:34])[C:26]=1[CH3:35])(=[O:24])=[O:23])[CH2:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][CH:17]=[CH:16]2)[CH2:5][O:6][C:7]([CH3:10])([CH3:9])[CH3:8].O[Li].O.Cl>CO.O1CCCC1.O>[NH:18]1[C:19]2[C:15](=[CH:14][C:13]([CH2:12][N:11]([S:22]([C:25]3[C:30]([CH3:31])=[CH:29][C:28]([O:32][CH3:33])=[C:27]([CH3:34])[C:26]=3[CH3:35])(=[O:24])=[O:23])[C@H:4]([CH2:5][O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[C:3]([OH:36])=[O:2])=[CH:21][CH:20]=2)[CH:16]=[CH:17]1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 2(R)-{(4-methoxy-2,3,6-trimethylbenzenesulfonyl)-[1H-indol-5-ylmethyl]amino}-3-tert-butoxypropionic acid methyl ester (1.0 g, 1.94 mmol) in 50% methanol/tetrahydrofuran (10 mL) was added a solution of LiOH.H2O (160 mg, 3.88 mmol) in water (1 mL). The reaction mixture was heated to 40° C. for 12 h and an additional amount of LiOH.H2O (160 mg, 3.88 mmol) in water (1 mL) was added. After 3 h, the aqueous solution was acidified to pH 3 using 2 N aqueous hydrochloric acid and the product was extracted into ethyl acetate. The combined ethyl acetate layers were dried over magnesium sulfate and concentrated to afford 2(R)-[(1H-indol-5-ylmethyl)-(4-methoxy-2,3,6-trimethylbenzene-sulfonyl)amino]-3-tert-butoxypropionic acid (0.90 g).

Workup

extractionthe product was extracted into ethyl acetate
dry with materialThe combined ethyl acetate layers were dried over magnesium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-1840f6744264468c964c40f2ab206699
Source dataset: uspto-grants-2005_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06844366B2

Reaction notes

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