Carbon Dioxide → HCID 15454946, compound

HRID 2287514Notes

Reaction equation

HRID 2287514 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C@H:15]([CH3:16])[C@H:14](OC(OCC2C=CC=CC=2)=O)[C@@H:13]([NH:28]C(OC(C)(C)C)=O)[C@:12]1(C)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[C:44](=O)=O.[OH-:47].[Na+]>CCOC(C)=O>[NH2:28][C@H:13]1[C@@H:14]([CH2:44][OH:47])[C@@H:15]([CH3:16])[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:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70307932HCID 70307932, compound

Product 1

HCID 15454946HCID 15454946, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of (2S*,3S*,4R*,5R*)-1-benzyloxycarb-onyl-4-(benzyloxycarbonyloxy)-methyl-3-[N-(t-butoxycarbonyl)-amino]-5-methyl-2-phenylpyrrolidine (0.80 g, 1,82 mmol) in AcOEt (15 ml) was added conc. HCl aq. (8.0 ml) at room temperature; on the addition evolution of CO2 gas took place. After stirring at room temperature for 1.5 hours, the reaction mixture was concentrated in vacuo to give a syrupy residue. This was basified to pH 10-11 with 20% NaOH aq. solution, and then extracted with AcOEt. The combined AcOEt extracts were washed with sat. NaCl aq. solution (×1), dried (K2CO3), and concentrated in vacuo to give title compound (0.61 g, 98%): IRmax (film): 3380(m), 1700(s), 1682(s), 1605(m), 1585(m), 1110(s), 750(m), 700(s) cm-1 ; 1H-NMR δ: 7.52-7.13(m, 9H), 6.99(br.s, 1H), 5.05(br.s, 3H), 4.92(d, J=8.1 Hz, 1H), 3.89(dd, J=10.4, 2.9 Hz, 1H), 3.76(dd, J=10.4, 10.4 Hz, 1H), 3.60-3.45 (m, 1H), 3.50(dd, J=11.2, 8.1 Hz, 1H), 2.10-1.70(m, 3H), 1.61(br.d, J=4.3 Hz, 3H) ppm. This was employed in the next step without further purification.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customto give a syrupy residue
  3. extractionextracted with AcOEt
  4. washThe combined AcOEt extracts were washed with sat. NaCl aq. solution (×1)
  5. dry with materialdried (K2CO3)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5d1237f4b3e645c593d9fc96b1a08dcd
Source dataset
uspto-grants-2000_07
Patent number
US06083943

Reaction notes

Loading…