Citric Acid → HCID 57692430, compound

HRID 1477374Notes

Reaction equation

HRID 1477374 reaction equation
[CH2:1]([N:8]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C@@H:9]([C@H:20]([CH2:28][CH:29]([OH:32])[CH2:30][OH:31])[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:40][S:41](Cl)(=[O:43])=[O:42].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>N1C=CC=CC=1>[CH2:1]([N:8]([CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[C@@H:9]([C@H:20]([CH2:28][CH:29]([OH:32])[CH2:30][O:31][S:41]([CH3:40])(=[O:43])=[O:42])[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 31297Methanesulfonyl chlorideHCID 57692426HCID 57692426, compound

Product 1

HCID 57692430HCID 57692430, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

1-benzyl 4-tert-butyl(2S,3S)-2-(dibenzylamino)-3-(2,3-dihydroxypropyl)succinate from step 1 j (2.917 g, 5.47 mmol) was dissolved in pyridine (10 mL), cooled to 0° C. and MsCl (0.444 mL, 5.74 mmol) was added. The solution was stirred at 0° C. for 4 hours and diluted by 10% citric acid. The reaction mixture was extracted with EtOAc three times. The combined organic solution was washed by 10% citric acid three times, then brine, dried with MgSO4 and concentrated, the residue was purified on silica gel using 50% EtOAc/Hexane as elution to provide of 1-benzyl 4-tert-butyl(2S,3S)-2-(dibenzylamino)-3-{2-hydroxy-3-[(methylsulfonyl)oxy]propyl}succinate (2.696 g, 81%). MS (ESI): 612.1.1 (M+H+).

Workup

  1. extractionThe reaction mixture was extracted with EtOAc three times
  2. washThe combined organic solution was washed by 10% citric acid three times
  3. dry with materialbrine, dried with MgSO4
  4. concentrationconcentrated
  5. customthe residue was purified on silica gel using 50% EtOAc/Hexane as elution

Sources & evidence

ORD record
ord-eda52415bbc74c299f61e0a8d9f70794
Source dataset
uspto-grants-2016_08
Patent number
US09403775B2

Reaction notes

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