4-(Nitrooxy)butan-1-ol → (S)-4-(nitrooxy)butyl 1-(9H-fluoren-9-yl)-13,13-dimethyl-3,11-dioxo-2,12-dioxa-4,10-diazatetradecane-5-carboxylate

HRID 1776965Notes

Reaction equation

FC1C([O:8][C:9](=O)[C@H:10]([CH2:29][CH2:30][CH2:31][CH2:32][NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[NH:11][C:12]([O:14][CH2:15][CH:16]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]3[C:17]2=[CH:18][CH:19]=[CH:20][CH:21]=3)=[O:13])=C(F)C(F)=C(F)C=1F.[N+:46]([O:49][CH2:50][CH2:51][CH2:52][CH2:53][OH:54])([O-:48])=[O:47]>CN(C=O)C>[CH:18]1[C:17]2[CH:16]([CH2:15][O:14][C:12](=[O:13])[NH:11][C@H:10]([C:9]([O:54][CH2:53][CH2:52][CH2:51][CH2:50][O:49][N+:46]([O-:48])=[O:47])=[O:8])[CH2:29][CH2:30][CH2:31][CH2:32][NH:33][C:34](=[O:35])[O:36][C:37]([CH3:38])([CH3:39])[CH3:40])[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]=2[CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Commercial N(α)-Fmoc-N(ε)-Boc-L-lysine pentafluorophenyl ester (6.51 mmol) and 4-(nitrooxy)-1-butanol (6.55 mmol) were dissolved in DMF (12 ml) and the mixture was cooled to 0° C. N,N-dimethylaminopyridine (DMAP) (6.55 mmol) were added and the reaction was slowly warmed to room temperature and stirred for 4 hours. Then the mixture was concentrate under reduced pressure and diluted with EtOAc, washed with 5% aqueous Na2HPO4 and brine.

Workup

temperaturethe reaction was slowly warmed to room temperature
concentrationThen the mixture was concentrate under reduced pressure
additiondiluted with EtOAc
washwashed with 5% aqueous Na2HPO4 and brine

Sources & evidence

ORD record: ord-f78d464e41044bd78c0c4750e92da70f
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266820B2

Reaction notes

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