Di-tert-butyl dicarbonate → (S)-4-Benzyl-3-((S)-3-(4-(benzyloxy)phenyl)-3-(isoxazol-3-yl)propanoyl)oxazolidin-2-one

HRID 2101754Notes

Reaction equation

HRID 2101754 reaction equation
[CH3:1][C:2](OC(OC(OC(C)(C)C)=O)=O)(C)C.[CH2:16]([C@H:23]1[CH2:27][O:26][C:25](=[O:28])[N:24]1[C:29](=[O:50])[CH2:30][C@@H:31]([C:36]1[CH:41]=[CH:40][C:39]([O:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[CH:38][CH:37]=1)[CH2:32][N+:33]([O-])=[O:34])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C1C=CN=CC=1)C.C(Br)=C>[CH2:16]([C@H:23]1[CH2:27][O:26][C:25](=[O:28])[N:24]1[C:29](=[O:50])[CH2:30][C@@H:31]([C:36]1[CH:37]=[CH:38][C:39]([O:42][CH2:43][C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)=[CH:40][CH:41]=1)[C:32]1[CH:2]=[CH:1][O:34][N:33]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 90495Di-tert-butyl dicarbonate2×HCID 57801835(S)-4-Benzyl-3-((S)-3-(4-(benzyloxy)phenyl)-4-nitrobutanoyl)oxazolidin-2-one

Product 1

HCID 57801834(S)-4-Benzyl-3-((S)-3-(4-(benzyloxy)phenyl)-3-(isoxazol-3-yl)propanoyl)oxazolidin-2-oneYield 93.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 11641BromoetheneSolvent

Procedure

(Boc)2O (6.9 g, 31.65 mmol) was added at room temperature to a solution of 6.3 (10 g, 21.1 mmol), vinyl bromide (230 mL, 1.0 M solution in THF), DMAP (256 mg, 2.1 mmol), and TEA (3.5 mL, 25.3 mmol). The mixture was stirred at room temperature for 2.5 days. During the reaction, more (Boc)2O (2×2 g) was added. After HPLC indicated that all 6.3 was consumed, the reaction mixture was placed in EtOAc (500 mL), and saturated NaHCO3 (400 mL) was added. The organic layer was separated, washed with brine, dried, and concentrated under vacuum. The crude product was placed in hot MeOH (70 mL). The mixture was stirred vigorously at 75° C. for 5 hours. The mixture was then cooled to room temperature and allowed to stand for 3 hours. The solid product was collected by filtration and washed with MeOH to give 6.4 (9.5 g). MS ESI (pos.) m/e: 483 (M+H). 1H NMR (CDCl3) δ 8.30(d, 1H), 7.30 (m, 12H), 6.95 (d, 2H), 6.15 (d, 1H), 5.05 (s, 2H), 4.76 (dd, 1H), 4.64 (m, 1H), 4.15 (d, 2H), 4.05 (dd, 1H), 3.56 (dd, 1H), 3.23 (dd, 1H), 2.78 (dd, 1H).

Workup

  1. additionwas added
  2. customwas consumed
  3. additionsaturated NaHCO3 (400 mL) was added
  4. customThe organic layer was separated
  5. washwashed with brine
  6. customdried
  7. concentrationconcentrated under vacuum
  8. stirringThe mixture was stirred vigorously at 75° C. for 5 hours
  9. temperatureThe mixture was then cooled to room temperature
  10. waitto stand for 3 hours
  11. filtrationThe solid product was collected by filtration
  12. washwashed with MeOH

Sources & evidence

ORD record
ord-16fc6cc0f39f4ee496e095209621cdf0
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

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