4-Methylmorpholine → t-Butyl (6R,7R)-7-Amino-3-[(RS)-tetrahydrofuran-3-yl]ceph-3-em-4-carboxylate

HRID 376579Notes

Reaction equation

HRID 376579 reaction equation
C1(CC([NH:10][C@@H:11]2[C:30](=[O:31])[N:13]3[C:14]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[C:15]([CH:18]4[CH2:22][CH2:21][O:20][CH2:19]4)[CH2:16][S:17][C@H:12]23)=O)C=CC=CC=1.CN1CCOCC1.P(Cl)(Cl)(Cl)(Cl)Cl>ClCCl.CO.O>[NH2:10][C@@H:11]1[C:30](=[O:31])[N:13]2[C:14]([C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])=[C:15]([CH:18]3[CH2:22][CH2:21][O:20][CH2:19]3)[CH2:16][S:17][C@H:12]12

Participants

7

Reactant 3

HCID 79724-MethylmorpholineHCID 24819Phosphorus pentachlorideHCID 54439270t-Butyl (6R,7R)-7-Phenylacetamido-3-[(RS)-tetra-hydrofuran-3-yl]ceph-3-em-4-carboxylate

Product 1

HCID 54127982t-Butyl (6R,7R)-7-Amino-3-[(RS)-tetrahydrofuran-3-yl]ceph-3-em-4-carboxylate

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

t-Butyl (6R,7R)-7-phenylacetamido-3-[(RS)-tetrahydrofuran-3-yl]ceph-3-em-4-carboxylate (0.9g) in dichloromethane (15ml) with N-methylmorpholine (0.45g, 0.49ml) was successively treated with phosphorus pentachloride (0.549g) in dichloromethane (13.74ml), methanol (10ml) and water (10ml) as described in Example 2(f). After purification by flash chromatography on silica gel eluting with 60, 80% ethyl acetate/hexane and then ethyl acetate, the title compound was obtained as a yellow solid (0.481g, 73%); (Found: M+, 326.1304. C15H22N2O4S requires M, 326.1300); vmax (CH2Cl2) 3408, 1775 and 1716cm-1 ; δH (CDCl3) 1.55 (9H, s), 1.69-2.41 (3H, m's), 3.31 and 3.48 with 3.34 and 3.49 (2H, 2ABq's, J 17.5 and 17.5Hz), 3.69-3.83 (4H, 2s's overlapping m), 3.97-4.05 (2H, m), 4.72 and 4.74 (1H, 2d's, J 4.3 and 4.4Hz) and 4.95 and 4.97 (1H, 2d's, J 4.3 and 4.4Hz).

Workup

  1. customAfter purification by flash chromatography on silica gel eluting with 60, 80% ethyl acetate/hexane

Sources & evidence

ORD record
ord-d02f029ed9ce4bb0840144a834ff93ae
Source dataset
uspto-grants-2000_02
Patent number
US06020329

Reaction notes

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