Hydrochloric Acid → HCID 71152421, compound

HRID 1497287Notes

Reaction equation

HRID 1497287 reaction equation
[C:1]([O:9][C@@H:10]1[C@H:15]2[NH:16][C:17](=[O:19])[O:18][C@H:14]2[CH2:13][C@H:12]([CH2:20][O:21][Si](C(C)(C)C)(C)C)[C@H:11]1[O:29][C:30](=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.CCOC(C)=O.CO>CO>[C:1]([O:9][C@@H:10]1[C@H:15]2[NH:16][C:17](=[O:19])[O:18][C@H:14]2[CH2:13][C@H:12]([CH2:20][OH:21])[C@H:11]1[O:29][C:30](=[O:37])[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21584119Ethylacetate methanolHCID 71152508HCID 71152508, compound

Product 1

HCID 71152421HCID 71152421, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of (3 aS,4R,5R,6R,7aS)-6-(((tert-butyldimethylsilyl)oxy)methyl)-2-oxooctahydrobenzo[d]oxazole-4,5-diyl dibenzoate (3.29 g, 6.27 mmol) in dry MeOH (50 mL) at room temperature was added a solution of HCl in 4:1 EtOAc-MeOH (1.5 M, 28 mL, 41.8 mmol). The mixture was stirred at room temperature for 2 h. The solvents were evaporated to give the crude product. This was purified by SiO2 column, eluted with 60-80% EtOAc in hexanes to give (3aS,4R,5R,6R,7aS)-6-(hydroxymethyl)-2-oxooctahydrobenzo[d]oxazole-4,5-diyl dibenzoate (1.87 g, 73%). MS m/z 434.1 (M+23, 100%); 1H NMR (400 MHz, CDCl3) δ 7.94 (d, J=7.8 Hz, 2H), 7.87 (d, J=7.8 Hz, 2H), 7.49 (t, J=7.8 Hz, 2H), 7.33 (t, J=7.8 Hz, 4H), 6.37 (s, 1H), 5.45 (dd, J=9.7 Hz, 6.8 Hz, 1H), 5.31 (t, J=10.0 Hz, 1H), 4.90-4.92 (m, 1H), 3.88 (t, J=6.8 Hz, 1H), 3.74 (dd, J=12.1 Hz, 2.5 Hz, 1H), 3.57 (dd, J=12.1 Hz, 2.0 Hz, 1H), 2.39 (d, J=13.8 Hz, 1H), 2.19-2.32 (m, 2H).

Workup

  1. customThe solvents were evaporated
  2. customto give the crude product
  3. customThis was purified by SiO2 column
  4. washeluted with 60-80% EtOAc in hexanes

Sources & evidence

ORD record
ord-9ad27f31c8f9431ea143207f02b1768f
Source dataset
uspto-grants-2015_12
Patent number
US09199949B2

Reaction notes

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