Ethanol → HCID 70285014, compound

HRID 1954457Notes

Reaction equation

HRID 1954457 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH:5]1[C:13]([OH:15])=[O:14])(=[O:3])[CH3:2].C(O)C.O.[C:20]1([C@H:26]([OH:31])[C@@H:27]([NH2:30])[CH2:28][OH:29])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CO>[C:20]1([C@H:26]([OH:31])[C@@H:27]([NH2:30])[CH2:28][OH:29])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][C@H:5]1[C:13]([OH:15])=[O:14])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 119881(S(R*,R*))-2-amino-1-phenylpropane-1,3-diolHCID 100587711-Acetyl-2-indolinecarboxylic acid

Product 1

HCID 70285014HCID 70285014, compoundYield 37.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

100 g N-acetyl-indoline-2-carboxylic acid (purity 96.5%) was dissolved in 835 ml of a mixture containing 90% ethanol (EtOH), 5% water and 5% methanol (MeOH), with heating to 60° C., and with mechanical stirring. 54.4 g/0.69 eq. (1S,2S)-1-phenyl-2-amino-1,3-propanediol ([α]20D =+25.7° (c=1, MeOH)) was dosed in portions in 30 min. at 60° C. At the end spontaneous crystallization of the salt took place. After 30 minutes' subsequent stirring at 60-66° C., cooling to 15° C. took place, followed by another 30 minutes' stirring. After filtration over a P4 glass filter, three washings with 120 ml EtOH took place. After air-drying, 68.9 g off-white (S)-N-acetyl-indoline-2-carboxylic acid-(1S,2S)-1-phenyl-2-amino-1,3-propanediol salt was obtained, corresponding to a yield of 37.8%. Enantiomeric excess=96.3% (chiral HPLC).

Workup

  1. customAt the end spontaneous crystallization of the salt
  2. temperaturecooling to 15° C.
  3. waitfollowed by another 30 minutes
  4. stirring' stirring
  5. filtrationAfter filtration over a P4 glass
  6. filtrationfilter
  7. washthree washings with 120 ml EtOH
  8. customAfter air-drying

Sources & evidence

ORD record
ord-9ea0bbcec59447c2aa6042f84a666ae7
Source dataset
uspto-grants-2000_09
Patent number
US06121460

Reaction notes

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