Trifluoroacetic acid → 2,5-Diamino-1,6-diphenyl-3-hydroxyhexane

HRID 850854Notes

Reaction equation

HRID 850854 reaction equation
C(OC([NH:8][CH:9]([CH:17]([OH:28])[CH2:18][CH:19]([NH2:27])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=O)(C)(C)C.FC(F)(F)C(O)=O.[OH-].[Na+]>C(Cl)Cl>[NH2:8][CH:9]([CH:17]([OH:28])[CH2:18][CH:19]([NH2:27])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 193651712-Tert-butoxycarbonylamino-3-hydroxy-5-amino-1,6-diphenylhexane

Product 1

HCID 187589802,5-Diamino-1,6-diphenyl-3-hydroxyhexane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2RS,3RS,5RS)-2-tert-Butoxycarbonylamino-3-hydroxy-5-amino-1,6-diphenylhexane obtained in Example 39 (A) was dissolved in methylene chloride (1 ml), and trifluoroacetic acid (0.5 ml) was added at room temperature. After the mixture was stirred at room temperature for 3 hours, a 10% aqueous sodium hydroxide was added. After being extracted with methylene chloride, the mixture was dried over anhydrous sodium sulfate. After the desiccant was filtered off, the filtrate was concentrated under reduced pressure to give the desired compound as a colorless solid (3.2 mg).

Workup

  1. extractionAfter being extracted with methylene chloride
  2. dry with materialthe mixture was dried over anhydrous sodium sulfate
  3. filtrationAfter the desiccant was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7a4f6e05e4f24290ac9d5c5cd74cce8b
Source dataset
uspto-grants-2000_01
Patent number
US06018069

Reaction notes

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