1,4-Dibromobutane → HCID 67494855, compound

HRID 1620382Notes

Reaction equation

C(N(CC)CC)C.Cl.[NH2:9][C@@H:10]([CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:11]([O:13][CH3:14])=[O:12].Br[CH2:25][CH2:26][CH2:27][CH2:28]Br>C(O)(C)(C)C>[C:20]([O:19][C:17]([NH:16][CH2:15][C@H:10]([N:9]1[CH2:28][CH2:27][CH2:26][CH2:25]1)[C:11]([O:13][CH3:14])=[O:12])=[O:18])([CH3:23])([CH3:22])[CH3:21]

Participants

Conditions

Temperature: 40 °C

Procedure

10 ml (65 mmol) of triethylamine are added to a solution of 5 g (20 mmol) of commercial methyl(S)-2-amino-3-tert-butoxycarbonylaminopropanoate hydrochloride in 150 ml of tert-butanol. The reaction medium is stirred for 20 min at 40° C. and then filtered in order to remove the triethylammonium salts. 3.8 ml (32 mmol) of 1,4-dibromobutane are added to the filtrate thus obtained, and the reaction medium is heated at 80° C. for 3 days. After the insoluble material has been filtered off, the filtrate is concentrated under vacuum. The residue obtained is purified by chromatography on a silica column, elution being carried out with a 98/2 dichloromethane/methanol mixture. 2.9 g (55%) of methyl(S)-3-tert-butoxycarbonylamino-2-pyrrolidin-1-ylpropanoate are obtained in the form of a yellow oil.

Workup

filtrationfiltered in order
customto remove the triethylammonium salts
customthus obtained
temperaturethe reaction medium is heated at 80° C. for 3 days
filtrationAfter the insoluble material has been filtered off
concentrationthe filtrate is concentrated under vacuum
customThe residue obtained
customis purified by chromatography on a silica column, elution

Sources & evidence

ORD record: ord-57935fb5044d479a9e2d951a1bde7db4
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772478B2

Reaction notes

Loading…