Lithium Hydroxide → HCID 67001363, compound

HRID 885702Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH:16]([NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C:17]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28][C:29]([O:31]C)=[O:30])=[CH:22][CH:21]=2)=[O:18])=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+]>C1COCC1.O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C@@H:16]([NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C:17]([NH:19][C:20]2[CH:21]=[CH:22][C:23]([CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[CH:24][CH:25]=2)=[O:18])=[N:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of methyl 4-(4-(3-(5-(benzyloxy)pyridin-2-yl)-2-(tert-butoxycarbonylamino)propanamido)phenyl)butanoate (0.59 g, 1.07 mmol) and lithium hydroxide (0.26 g, 10.7 mmol) in 10 mL THF/H2O (1:1) was heated at 60° C. for 2 h (monitored by TLC). The solution was acidified to PH=2 and extracted with dichloromethane. The dichloromethane was separated, dried over magnesium sulfate, and concentrated in vacao to give 0.51 g of the desired compound (90%): (400 MHz in CDCl3, Bruker AVANCE-400): δ 1.30 (s, 9H, Boc), 1.74 (m, 2H, CH2), 2.17 (t, 2H, CH2—CH2—COOMe, J=7.34 Hz), 2.52 (t, 2H, CH2, J=7.55 Hz), 2.92-3.07 (m, 2H, CH2), 4.44 (m, 1H CH), 5.13 (s, 2H OBn), 7.09 (d, 1H, J=8.47 Hz, Ar—H), 7.21 (d, 1H, Ar—H, J=8.52 Hz), 7.31˜7.48 (m, 9H Ar—H), 8.26 (br, 1H, NH), 9.91 (br, 1H, OH).

Workup

extractionextracted with dichloromethane
customThe dichloromethane was separated
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacao

Sources & evidence

ORD record: ord-db5b22d90b8f4b2f85cbe5d6a7ef6741
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242282B2

Reaction notes

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