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Hydrochloric Acid → (2S,3S)-2-amino-3-methyl-valeric acid N-{2-[3-methoxy-4-(naphthalen-1-ylmethoxy)-phenyl]-ethyl}-amide

HRID 650982
Notes
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Reaction equation

HRID 650982 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:21][CH2:22][NH:23][C:24](=[O:38])[C@@H:25]([NH:30]C(OC(C)(C)C)=O)[C@@H:26]([CH3:29])[CH2:27][CH3:28])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1.Cl.O>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:21][CH2:22][NH:23][C:24](=[O:38])[C@@H:25]([NH2:30])[C@@H:26]([CH3:29])[CH2:27][CH3:28])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 56999350(2S,3S)-2-(tert-butoxycarbonyl-amino)-3-methyl-valeric acid N-{2-[3-methoxy-4-(naphthalen-1-ylmethoxy)-phenyl]-ethyl}-amide

Product 1

HCID 57011389(2S,3S)-2-amino-3-methyl-valeric acid N-{2-[3-methoxy-4-(naphthalen-1-ylmethoxy)-phenyl]-ethyl}-amide

Reagents, catalysts & solvents 1

HCID 31275
1,4-Dioxane
Solvent
2×

Procedure

12.6 9 of (2S,3S)-2-(tert-butoxycarbonyl-amino)-3-methyl-valeric acid N-{2-[3-methoxy-4-(naphthalen-1-ylmethoxy)-phenyl]-ethyl}-amide are dissolved in 100 ml of dioxane. 200 ml of a 4M solution of hydrogen chloride in dioxane are added thereto. The reaction mixture is stirred at room temperature for 24 hours and then 300 ml of water are added thereto. Extraction is carried out twice using 300 ml of ethyl acetate each time. The organic phases are washed twice using 150 ml of 2N hydrochloric acid each time. The combined aqueous extracts are adjusted to a pH value of >8 by the addition of solid potassium carbonate. Extraction is carried out twice using 400 ml of tert-butyl methyl ether each time. The organic phases are combined, dried over potassium carbonate and concentrated, yielding (2S,3S)-2-amino-3-methyl-valeric acid N-{2-[3-methoxy-4-(naphthalen-1-ylmethoxy)-phenyl]-ethyl}-amide in the form of a yellow oil.

Workup

  1. extractionExtraction
  2. washThe organic phases are washed twice
  3. additionThe combined aqueous extracts are adjusted to a pH value of >8 by the addition of solid potassium carbonate
  4. extractionExtraction
  5. dry with materialdried over potassium carbonate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c7cb782e77d34d9bbf6cfc5e29e5992c
Source dataset
uspto-grants-2001_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06277849B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes