HuagongsheHuagongshe Chemistry Print Report · For research reference only
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
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Bromide | HCID 253877 | — |
| Reactant | (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 ester | HCID 44516526 | — |
| Reactant | sodium (3aR,6E,7R,7aS)-7-acetamido-6-hydroxyimino-2,2-dimethyl-7,7a-dihydro-3aH-1,3-benzodioxole-4-carboxylate | HCID 52917780 | — |
| Reactant | (3R,4R,5S)-4-Acetylamino-5-tert-butoxycarbonylamino-3-hydroxy-cyclohex-1-enecarboxylic acid ethyl ester | HCID 68364405 | — |
| Reactant | (3aR,7R,7aS)-ethyl-7-acetamido-6-(hydroxyimino)-2,2-dimethyl-3a,6,7,7a-tetrahydrobenzo[d][1,3]dioxole-4-carboxylate | HCID 86671844 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Dichloromethane methanol | HCID 21226129 | — |
| Product | Sodium (3aR,6R,7R,7aS)-7-acetamido-6-hydroxy-2,2-dimethyl-3a,6,7,7a-tetrahydrobenzo[d][1,3]dioxole-4-carboxylate | HCID 86671843 | — |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08716333B2 |
| Source dataset | uspto-grants-2014_05 |
| ORD ID | ord-4112cb3c119344b89f4e86f2a192b42c |
| Source note | uspto-grants-2014_05 |