Hydrochloric Acid → HCID 69651958, compound

HRID 1987174Notes

Reaction equation

HRID 1987174 reaction equation
C([O:3][C:4]([C@@H:6]1[C@@H:10]([C:11](=[O:20])[NH:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[CH2:9][N:8]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:7]1)=[O:5])C.Cl>C1COCC1.O.C(OCC)(=O)C>[C:24]([O:23][C:21]([N:8]1[CH2:9][C@H:10]([C:11](=[O:20])[NH:12][C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)[C@@H:6]([C:4]([OH:5])=[O:3])[CH2:7]1)=[O:22])([CH3:27])([CH3:25])[CH3:26]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 690476271-(1,1-Dimethylethyl) 3-ethyl (3R,4R)-4-[[(4-chlorophenyl)amino]carbonyl]-1,3-pyrrolidinedicarboxylate

Product 1

HCID 69651958HCID 69651958, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
25 °C

Procedure

The ester obtained from step 2a (4.07 g; 10.3 mmol) is dissolved in a mixture of THF/water (1:1; 40 ml). LiOH monohydrate (0.947 g; 22.6 mmol) is added to the mixture and complete saponification is obtained after stirring for 18 h at 25° C. The mixture is acidified with 1N aq. HCl and diluted with ethyl acetate (100 ml). The organic phase is washed with brine (100 ml) and dried over Na2SO4. The organic phase is filtered and the filtrate is evaporated to dryness. Yield: 3.28 g (86.7%), ESI-MS: m/z=367 [M−H]−, Cl-pattern

Workup

  1. customcomplete saponification is obtained
  2. washThe organic phase is washed with brine (100 ml)
  3. dry with materialdried over Na2SO4
  4. filtrationThe organic phase is filtered
  5. customthe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-c78f9c228a384773ae52d0358cf2bec3
Source dataset
uspto-grants-2009_06
Patent number
US07550487B2

Reaction notes

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