Triethylamine → HCID 86731577, compound

HRID 335495Notes

Reaction equation

HRID 335495 reaction equation
[CH2:1]([N:3]([C:11]1[S:12][C@H:13]2[O:19][C@@H:18]3[CH2:20][O:21][CH:22]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[O:23][C@H:17]3[C@H:16]([OH:30])[C@H:14]2[N:15]=1)[C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7])[CH3:2].[CH3:31][S:32](Cl)(=[O:34])=[O:33].C(N(CC)CC)C.CCOC(C)=O>C(Cl)Cl>[CH3:31][S:32]([O:30][C@@H:16]1[C@H:14]2[N:15]=[C:11]([N:3]([C:4]([O:5][C:6]([CH3:9])([CH3:7])[CH3:8])=[O:10])[CH2:1][CH3:2])[S:12][C@H:13]2[O:19][C@@H:18]2[CH2:20][O:21][CH:22]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[O:23][C@@H:17]12)(=[O:34])=[O:33]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 71271218HCID 71271218, compound

Product 1

HCID 86731577HCID 86731577, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl ethyl[(3aR,4aR,8aS,9R,9aR)-9-hydroxy-7-phenyl-3a,4a,5,8a,9,9a-hexahydro[1,3]dioxino[4′,5′:5,6]pyrano[3,2-d][1,3]thiazol-2-yl]carbamate (199.00 mg; 0.46 mmol; 1.00 eq.) in DCM (2.00 ml) was added methanesulfonyl chloride (0.05 ml; 0.68 mmol; 1.50 eq.) and N,N-diethylethanamine (0.09 ml; 0.68 mmol; 1.50 eq.). The reaction was stirred at room temperature for 2 h. The desired product was isolated by flash chromatography (KPNH, 20 to 75% EtOAc/Hex) to afford (3aR,4aR,8aR,9R,9aR)-2-[(tert-butoxycarbonyl)(ethyl)amino]-7-phenyl-3a,4a,5,8a,9,9a-hexahydro[1,3]dioxino[4′,5′:5,6]pyrano[3,2-d][1,3]thiazol-9-yl methanesulfonate (90 mg, 38%) as a white solid (once lyophilized).

Sources & evidence

ORD record
ord-d86e55b6d1d54cd9b20333bb6ce561df
Source dataset
uspto-grants-2014_11
Patent number
US08884023B2

Reaction notes

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