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Sulfuric Acid → (S)-2-(((Benzyloxy)carbonyl)amino)-5-((diphenyl(p-tolyl)methyl)amino)-5-oxopentanoic acid

HRID 2209860
Notes
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Reaction equation

HRID 2209860 reaction equation
[NH:1]([C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH2:6].[CH3:21][C:22]1[CH:27]=[CH:26][C:25]([C:28](O)([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:24][CH:23]=1.C(OC(=O)C)(=O)C.S(=O)(=O)(O)O>C(O)(=O)C>[NH:1]([C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH:6][C:28]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:25]1[CH:24]=[CH:23][C:22]([CH3:21])=[CH:27][CH:26]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 75855L-Glutamine, N2-[(phenylmethoxy)carbonyl]-HCID 951454-Methyltriphenylcarbinol

Product 1

HCID 90470049(S)-2-(((Benzyloxy)carbonyl)amino)-5-((diphenyl(p-tolyl)methyl)amino)-5-oxopentanoic acid

Reagents, catalysts & solvents 1

HCID 176
Acetic Acid
Solvent

Procedure

A mixture of 140.14 g Z-Gln-OH (0.5 mole) and 274.4 g 4-methyltriphenylcarbinol (1 mole) in 1.5 l acetic acid and 93.4 ml acetic anhydride (1 mole) is stirred at room temperature for 7 minutes. Upon addition of 2.5 ml concentrated sulfuric acid the temperature is raised to 50° C.; a clear, yellow solution results after 15 minutes. After 21/2 hrs the solution is allowed to cool and poured into 5 l ice-cold water. The precipitate formed is filtered off, washed thoroughly with water and dissolved in 1 l ethylacetate. The resulting solution is washed with saturated brine, dried over sodium sulfate and concentrated under reduced pressure to an oil (400 ml) which crystallized on addition of diisopropylether.

Workup

  1. temperatureis raised to 50° C.
  2. customa clear, yellow solution results after 15 minutes
  3. custom2 hrs
  4. temperatureto cool
  5. customThe precipitate formed
  6. filtrationis filtered off
  7. washwashed thoroughly with water
  8. dissolutiondissolved in 1 l ethylacetate
  9. washThe resulting solution is washed with saturated brine
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated under reduced pressure to an oil (400 ml) which
  12. customcrystallized on addition of diisopropylether

Sources & evidence

ORD record
ord-04c001aad7b0452e9625311106094da6
Source dataset
uspto-grants-1995_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05455363

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes