Potassium Bromide → HCID 76078659, compound

HRID 1955083Notes

Reaction equation

C([O:8][NH:9][C:10]([CH2:12][N:13]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:14](=[O:25])[CH2:15][CH:16]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:17]([NH:19][CH3:20])=[O:18])=[O:11])C1C=CC=CC=1.[K+].[Br-]>>[OH:8][NH:9][C:10]([CH2:12][N:13]([CH2:26][CH:27]([CH3:29])[CH3:28])[C:14](=[O:25])[CH2:15][CH:16]([CH2:21][CH:22]([CH3:23])[CH3:24])[C:17]([NH:19][CH3:20])=[O:18])=[O:11]

Participants

Reactant 2

HCID 253877Potassium Bromide

HCID 53951753HCID 53951753, compound

Product 1

HCID 76078659HCID 76078659, compound

Procedure

N4 -(Benzyloxycarbamoyl-methyl)-2,N4 -diisobutyl-N1 -methyl-succinamide (0.30 g, 0.74 mmol) was deprotected by catalytic hydrogenolysis as described in Example 30 (Step 1) then purified by column chromatography (silica gel, 5% methanol in dichloromethane) to give the product as a white hygroscopic solid. m.p. 60.5-61.5° C. 1H-NMR; δ(CD3OD), 4.16-3.62 (2H, br m), 3.31-2.82 (2H, br m), 2.69 (1H, m), 2.58 (4H, m), 2.30 (1H, m), 1.82 (1H, m), 1.42 (2H, m), 1.18 (1H, m) and 0.78 (1 2H, br m). 13C-NMR; δ(CD3OD), 178.6, 178.4, 174.7, 174.5, 168.3, 167.9, 57.5, 55.4, 48.6, 43.1, 43.0, 42.6, 42.3, 37.0, 32.7, 28.9, 28.0, 27.0, 26.3, 23.6, 23.3, 22.6, 20.5, 20.3 and 14.4. IR (KBr) νmax 3309, 2957, 2871, 1681, 1636, 1560 and 1490 cm-1.

Workup

customthen purified by column chromatography (silica gel, 5% methanol in dichloromethane)
customto give the product as a white hygroscopic solid

Sources & evidence

ORD record: ord-3f241d7c84c44c3fb60e513364fad4ed
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06124329

Reaction notes

Loading…