4,4-Diethoxybutylamine → HCID 178467802, compound

HRID 981333Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]=[C:9]([NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([NH:19][CH:20]([O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])[C:21](OC)=[O:22])=[O:18])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:41]([O:43][CH:44]([O:49][CH2:50][CH3:51])[CH2:45][CH2:46][CH2:47][NH2:48])[CH3:42]>C1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]=[C:9]([NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17](=[O:18])[NH:19][CH:20]([O:25][Si:26]([C:29]([CH3:30])([CH3:31])[CH3:32])([CH3:27])[CH3:28])[C:21](=[O:22])[NH:48][CH2:47][CH2:46][CH2:45][CH:44]([O:43][CH2:41][CH3:42])[O:49][CH2:50][CH3:51])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 38 °C

Procedure

1.80 g (3.06 mmol) of methyl 7-[2,3-bis(t-butoxycarbonyl)-guanidino]heptanoyl-α-t-butyldimethylsilyloxyglycinate and 0.542 g (3.36 mmol) of 4-aminobutyraldehyde diethyl acetal were dissolved in 5.6 ml of benzene and stirred at 38° C. for 51 hours. Then the solvent was distilled off under reduced pressure and the oily substance thus obtained was subjected to column chromatography with the use of Silica gel 60 (mfd by Merck Co. & Inc.). By eluting with chloroform/ethyl acetate (3:2, v/v), 1.39 g of the aimed compound was obtained in the form of an oily product (yield 63.3%).

Workup

distillationThen the solvent was distilled off under reduced pressure
customthe oily substance thus obtained
washBy eluting with chloroform/ethyl acetate (3:2

Sources & evidence

ORD record: ord-c4a44b497c054cd597265e35bc5dc99f
Source dataset: uspto-grants-1991_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04990536

Reaction notes

Loading…