Sodium Chloride → HCID 87567437, compound

HRID 2054780Notes

Reaction equation

HRID 2054780 reaction equation
[Si]([O:8][CH2:9][CH:10]([N:18]([CH:26]=[O:27])[C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(C(C)(C)C)(C)C.C1COCC1.O.[Na+].[Cl-].C([O-])(O)=O.[Na+]>C(O)(=O)C>[OH:8][CH2:9][CH:10]([N:18]([CH:26]=[O:27])[C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:22])[CH3:23])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 516892Sodium BicarbonateHCID 21881883Oxolane--water (1/1)HCID 87567414HCID 87567414, compound

Product 1

HCID 87567437HCID 87567437, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

tertbutyl 3-(tert-butyldimethylsilyloxy)-1-oxo-1-phenylpropan-2-lmethylcarbamate (36) (640 mg, 1.6 mmol, 1.0 equiv.) was added to a 100 mL RBF followed by a 1:1 mixture of THF/H2O (8 mL). The mixture was stirred and glacial acetic acid (12 mL) was added to the reaction flask. The reaction stirred for 20 h at rt. The reaction was transferred to a 250 mL separatory funnel with sat. NaCl (50 mL) and sat. NaHCO3 (50 mL). The aqueous layer was extracted with EtOAc (3×70 mL) and the combined organic layers were dried over Na2SO4. The solution was then concentrated on a rotary evaporator and dried under vacuum to give 550 mg of crude material. The residue was purified by flash column chromatography (50% EtOAc/hexanes) to give 440 mg (97%) of 37 as a colorless oil. Rf=0.33 (50% EtOAc/hexanes); IR (film) 3451, 2975, 1681, 1149 cm−1; 1H NMR (500 MHz, CDCl3) δ Major rotamer: 7.96 (d, J=7.5 Hz, 1H, Ph-H), 7.90 (d, J=7.5 Hz, 1H, Ph-H), 7.58 (t, J=6.5 Hz, 1H, Ph-H), 7.46 (m, 2H, Ph-H), 5.45 (t, J=6.0 Hz, 1H, Boc-N—CH), 4.24 (m, 1H, CH—CH2), 4.14 (m, 1H, CH—CH2), 2.72 (s, 3H, Boc-N—CH3), 2.50 (m, 1H, CH2—OH), 1.43 (s, 9H, Boc-t-butyl-CH3). Minor rotamer: 4.89 (t, J=6.0 Hz, 1H, Boc-N—CH), 3.94 (m, 1H, CH—CH2), 3.81 (m, 1H, CH—CH2), 2.90 (s, 3H, Boc-N—CH3), 1.38 (s, 9H, Boc-t-butyl-CH3); 13C NMR (125 MHz, CDCl3) δ 199.9, 199.2, 156.1, 154.6, 135.7, 133.8, 128.9, 128.8, 128.5, 128.3, 81.7, 80.9, 63.5, 61.0, 60.8, 60.7, 33.3, 32.1, 28.4, 28.3; LRMS (ESI-MS m/z): Mass calcd for C15H21NO4Na [M+Na+], 302.32. Found 302.

Workup

  1. stirringThe reaction stirred for 20 h at rt
  2. extractionThe aqueous layer was extracted with EtOAc (3×70 mL)
  3. dry with materialthe combined organic layers were dried over Na2SO4
  4. concentrationThe solution was then concentrated on a rotary evaporator
  5. customdried under vacuum
  6. customto give 550 mg of crude material
  7. customThe residue was purified by flash column chromatography (50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-ecc2939899f146d292dc6a3f582b01d1
Source dataset
uspto-grants-2008_02
Patent number
US07329775B2

Reaction notes

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