Potassium Bromide → Sodium (3aR,6R,7R,7aS)-7-acetamido-6-hydroxy-2,2-dimethyl-3a,6,7,7a-tetrahydrobenzo[d][1,3]dioxole-4-carboxylate

HRID 1020391Notes

Reaction equation

HRID 1020391 reaction equation
[K+].[Br-].C([O:5][C:6]([C:8]1[C@@H:16]2[C@@H:12]([O:13][C:14]([CH3:18])([CH3:17])[O:15]2)[C@H:11]([NH:19][C:20](=[O:22])[CH3:21])[C:10](=NO)[CH:9]=1)=[O:7])C.C(N[C@H]1[C@@H]2OC(C)(C)O[C@@H]2C(C([O-])=O)=C/C/1=N\O)(=[O:27])C.[Na+:45].C(OC(C1C[C@H](NC(OC(C)(C)C)=O)[C@@H](NC(=O)C)[C@H](O)C=1)=O)C.C(OC(C1[C@@H]2[C@@H](OC(C)(C)O2)[C@H](NC(=O)C)[C@@H](NC(OC(C)(C)C)=O)C=1)=O)C>CO.C(Cl)Cl.CO>[C:20]([NH:19][C@H:11]1[C@@H:12]2[O:13][C:14]([CH3:18])([CH3:17])[O:15][C@@H:16]2[C:8]([C:6]([O-:5])=[O:7])=[CH:9][C@H:10]1[OH:27])(=[O:22])[CH3:21].[Na+:45]

Participants

8

Reactant 5

HCID 253877Potassium BromideHCID 44516526(3aR,6S,7R,7aS)-7-Acetylamino-6-tert-butoxycarbonylamino-2,2-dimethyl-3a,6,7,7a-tetrahydro-benzo[1,3]dioxole-4-carboxylic acid ethyl esterHCID 52917780sodium (3aR,6E,7R,7aS)-7-acetamido-6-hydroxyimino-2,2-dimethyl-7,7a-dihydro-3aH-1,3-benzodioxole-4-carboxylateHCID 68364405(3R,4R,5S)-4-Acetylamino-5-tert-butoxycarbonylamino-3-hydroxy-cyclohex-1-enecarboxylic acid ethyl esterHCID 86671844(3aR,7R,7aS)-ethyl-7-acetamido-6-(hydroxyimino)-2,2-dimethyl-3a,6,7,7a-tetrahydrobenzo[d][1,3]dioxole-4-carboxylate

Product 1

HCID 86671843Sodium (3aR,6R,7R,7aS)-7-acetamido-6-hydroxy-2,2-dimethyl-3a,6,7,7a-tetrahydrobenzo[d][1,3]dioxole-4-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

RF=0.15 (DCM/MeOH 3/1); [α]D20=−57.471 (c 0.5, MeOH); IR (KBr) ν 3419, 2929, 1691, 1595, 1552, 1384, 1240, 1214, 1045, 869 cm−1; 1H NMR (300 MHz, MeOD) δ 8.00 (d, 1H, J=7.5 Hz), 6.97 (d, 1H, J=3.9 Hz), 5.01 (d, 1H, J=5.4 Hz), 4.44 (t, 1H, J=3.9 Hz), 4.42-4.31 (m, 2H), 2.01 (s, 3H), 1.39 (s, 1H) ppm; 13C NMR (75 MHz, MeOD) δ 172.7, 109.1, 73.8, 70.5, 64.0, 51.8, 26.6, 24.7, 21.2 ppm; MS (FAB+) m/z %: 294 (M+H) (8), 272 (M−Na++2H+) (100), 214 (85), 176 (17), 126 (12), 84 (7), 60 (10), 43 (26); HRMS Calc'd for C12H18NO6: 272.11341 found: 272.11381.

Sources & evidence

ORD record
ord-4112cb3c119344b89f4e86f2a192b42c
Source dataset
uspto-grants-2014_05
Patent number
US08716333B2

Reaction notes

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