Lithium Hydroxide → HCID 22147932, compound

HRID 1823928Notes

Reaction equation

HRID 1823928 reaction equation
C[O:2][C:3](=[O:22])[CH:4]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=1)[CH2:5][NH:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[OH-].[Li+]>O1CCCC1.O>[C:10]([O:9][C:7]([NH:6][CH2:5][CH:4]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([Cl:21])[CH:15]=1)[C:3]([OH:22])=[O:2])=[O:8])([CH3:13])([CH3:11])[CH3:12]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 23570950HCID 23570950, compound

Product 1

HCID 22147932HCID 22147932, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To 3-tert-Butoxycarbonylamino-2-(3,4-dichloro-phenyl)-propionic acid methyl ester (17.11 g, 0.049 mol) in tetrahydrofuran-water (200 ml of each) was added lithium hydroxide (1.18 g, 0.049 mol). The reaction mixture was stirred at room temperature for 6 hours. THF was removed in vacuo and the pH was adjusted to pH 4 with 2M hydrochloric acid. The aqueous phase was extracted with EtOAc (3×100 ml). The combined organic phases were dried (MgSO4) and concentrated in vacuo. The title compound was obtained as a foam in 89% yield (14.67 g). 1H NMR (400 MHz, DMSO-d6) δ 1.30 (9H, s), 3.22–3.35 (1H, m), 3.35–3.50 (1H, m), 3.76 (1H, t), 6.84 (1H, t), 7.24 (1H, m); 7.48 (1H, s), 7.58 (1H, d), 12.85 (1H, s); MS (ES+): m/e=334.2 (8%); MS (ES−): m/e=332.2 (100%), 334.1 (65%), 336.1 (10%).

Workup

  1. customTHF was removed in vacuo
  2. extractionThe aqueous phase was extracted with EtOAc (3×100 ml)
  3. dry with materialThe combined organic phases were dried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7d73e3cc7bc3438d82eac90ddf224bd7
Source dataset
uspto-grants-2006_05
Patent number
US07041687B2

Reaction notes

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