Hexamethylphosphoramide → HCID 10961504, compound

HRID 336212Notes

Reaction equation

C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[C:11]1([C@@H:17]2[N:22]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:21][C:20](=[O:30])[O:19][C@@H:18]2[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Cl:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42]I.CN(P(N(C)C)(N(C)C)=O)C>C1COCC1.CCOC(C)=O>[C:26]([O:25][C:23]([N:22]1[C@@H:17]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C@@H:18]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[O:19][C:20](=[O:30])[C@@H:21]1[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][Cl:37])=[O:24])([CH3:29])([CH3:27])[CH3:28]

Participants

Conditions

Temperature: -78 °C

Procedure

A 1.0M solution of sodium bis(trimethylsilyl)amide in THF (55.0 mL, 55.2 mmol) is added at −78° C. to a solution of (5S,6R)-5,6-diphenyl-4-tert-butoxycarbonyl-morpholin-2-one (13.0 g, 36.8 mmol), 1-chloro-5-iodo-pentane (25.0 g, 108.0 mmol) and HMPA (55.0 mL) in THF (200.0 mL). The reaction mixture is stirred at −78° C. for 2 hours and at room temperature for 1 hour. The reaction mixture is diluted with EtOAc, washed with water and brine. After drying the organic phase over anhydrous Na2SO4, the solvent is removed under reduced pressure to afford the crude product that is purified by silica gel column chromatography to afford the title compound; m/z 358 [M-Boc+H].

Workup

washwashed with water and brine
dry with materialAfter drying the organic phase over anhydrous Na2SO4
customthe solvent is removed under reduced pressure
customto afford the crude product that
customis purified by silica gel column chromatography

Sources & evidence

ORD record: ord-a314b8452555435e9290bcb694219f81
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889670B2

Reaction notes

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