Carbon Dioxide → HCID 15454918, compound

HRID 2287529Notes

Reaction equation

HRID 2287529 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C@H:15]([CH3:16])[C@H:14](COCC2C=CC=CC=2)[C@H:13]([NH:26]C(OC(C)(C)C)=O)[C@@H:12]1[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:40](=[O:42])=[O:41].[CH3:43]O>Cl>[NH2:26][C@H:13]1[CH2:14][C@H:16]([C:40]([O:42][CH3:43])=[O:41])[CH2:15][N:11]([C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[C@H:12]1[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 887MethanolHCID 15454940HCID 15454940, compound

Product 1

HCID 15454918HCID 15454918, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of (2S*,3S*,5S*)-1-benzyloxycarbonyl-3-(N-tert-butoxycarbonyl)amino-5-methoxycarbonyl-2-phenylpiperidine (1.01 g, 2.16 mmol) in Hydrogen Chloride, Methanol Reagent 10 (20.0 ml) was stirred and heated at reflux for 10 minutes; the reaction mixture became homogeneous with evolution of CO2 gas. This mixture was concentrated in vacuo, and the syrupy residue was basified with sat. Na2CO3 aq. solution. The mixture was extracted with CH2Cl2 (×4). The combined CH2Cl2 extracts were dried (Na2SO4), and concentrated in vacuo to give crude title compound (0.789 g, quantitative) as a pale yellow syrup. IRmax (film): 3375(m), 3310(w), 1730(br., s), 1700(br., s), 1603(m), 1585(m), 1497(s), 1122(s), 740(s), 700(s) cm-1 ; 1H-NMR δ: 7.45-7.15(m, 10H), 5.26(d, J=5.9 Hz, 1H), 5.15(d, J=12.5 Hz, 1H), 5.01(d, J=12.5 Hz, 1H), 4.51(dd, J=13.9, 2.1 Hz, 1H), 3.65(s, 3H), 3.56-3.43(m, 1H), 3.54(dd, J=13.9, 4.2 Hz, 1H), 2.95-2.85(m, 1H), 2.22(ddd, J=14.9, 4.0, 4.0 Hz, 1H), 1.95(ddd, J=14.9, 10.9, 6.6 Hz, 1H) ppm.

Workup

  1. temperatureheated
  2. temperatureat reflux for 10 minutes
  3. concentrationThis mixture was concentrated in vacuo
  4. extractionThe mixture was extracted with CH2Cl2 (×4)
  5. dry with materialThe combined CH2Cl2 extracts were dried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-192c0f67fa64483ab15dc55d67853c30
Source dataset
uspto-grants-2000_07
Patent number
US06083943

Reaction notes

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