Diphosgene → HCID 86700680, compound

HRID 1406863Notes

Reaction equation

O=C(Cl)[O:3][C:4](Cl)(Cl)[Cl:5].[CH:9]1[C:21]2[CH:20]([CH2:22][O:23][C:24]([N:26]3[CH2:31][CH2:30][CH:29]([C:32]4[O:36][N:35]=[C:34]([C@@H:37]5[CH2:42][CH2:41][C@@H:40]([NH:43][O:44][CH2:45][C:46]6[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=6)[CH2:39][N:38]5[C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[N:33]=4)[CH2:28][CH2:27]3)=[O:25])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]=2[CH:12]=[CH:11][CH:10]=1>C(Cl)Cl>[CH:18]1[C:19]2[CH:20]([CH2:22][O:23][C:24]([N:26]3[CH2:27][CH2:28][CH:29]([C:32]4[O:36][N:35]=[C:34]([C@@H:37]5[CH2:42][CH2:41][C@@H:40]([N:43]([O:44][CH2:45][C:46]6[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=6)[C:4]([Cl:5])=[O:3])[CH2:39][N:38]5[C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[N:33]=4)[CH2:30][CH2:31]3)=[O:25])[C:21]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:14]=2[CH:15]=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Diphosgene (144 mg, 0.727 mmol) was added to a solution of (2S,5R)-tert-butyl 2-(5-(1-(((9H-fluoren-9-yl)methoxy) carbonyl)piperidin-4-yl)-1,2,4-oxadiazol-3-yl)-5-(benzyloxyamino)piperidine-1-carboxylate (380 mg, 0.559 mmol) and TEA (113 mg, 1.118 mmol) in DCM (5.0 mL). The mixture was stirred at 0° C. for 1 h, then, DCM (20 mL) was added and the mixture was washed with saturated sodium chloride (2×), dried over Na2SO4, and concentrated to give (2S,5R)-tert-butyl 2-(5-(1-(((9H-fluoren-9-yl)methoxy)carbonyl)piperidin-4-yl)-1,2,4-oxadiazol-3-yl)-5-(benzyloxy(chlorocarbonyl)amino)piperidine-1-carboxylate (400 mg), which was directly used in the next step. ESI-MS (EI+, m/z): 742 [M+H]+.

Workup

washthe mixture was washed with saturated sodium chloride (2×)
dry with materialdried over Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-5b65d205f6a84d2abfd0339c0a67840a
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916709B2

Reaction notes

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