Triethylamine → N-[[1,2,3,4-Tetrahydro-2-[[(t-butyl)thio]methyl]-2-naphthalenyl]carbonyl]-L-alanine, benzyl ester

HRID 1656049

Reaction equation

HRID 1656049 reaction equation
[C:1]([C:4]1([CH2:14][S:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5]1)([OH:3])=O.Cl.CN(C)CCCN=C=NCC.Cl.[CH2:33]([O:40][C:41](=[O:45])[C@H:42]([CH3:44])[NH2:43])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(N(CC)CC)C>O1CCCC1>[C:16]([S:15][CH2:14][C:4]1([C:1]([NH:43][C@H:42]([C:41]([O:40][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:45])[CH3:44])=[O:3])[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5]1)([CH3:19])([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12210893L-Alanine, phenylmethyl ester, hydrochloride (1:1)HCID 197899372-Carboxy-2-(t-butyl)thiomethyl-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 131718217N-[[1,2,3,4-Tetrahydro-2-[[(t-butyl)thio]methyl]-2-naphthalenyl]carbonyl]-L-alanine, benzyl esterYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 2-carboxy-2-(t-butyl)thiomethyl-1,2,3,4-tetrahydronaphthalene (278 mg, 1.0 mmol) in anhydrous tetrahydrofuran (10 mL). Add 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (230 mg, 1.2 mmol), L-alanine benzyl ester hydrochloride (216 mg, 1.00 mmol) and triethylamine (0.132 mL, 1.00 mmol). Stir at room temperature under an argon atmosphere overnight. Partition between ethyl ether and 5% sulfuric acid. Separate the organic phase and wash with water, saturated sodium hydrogen carbonate and brine. Dry (MgSO4) and evaporate the solvent in vacuo. Purify by silica gel chromatography (20% ethyl acetate/hexane) to give the title compound as a clear yellow oil (210 mg, 48%).

Workup

  1. customPartition between ethyl ether and 5% sulfuric acid
  2. customSeparate the organic phase
  3. washwash with water, saturated sodium hydrogen carbonate and brine
  4. dry with materialDry (MgSO4)
  5. customevaporate the solvent in vacuo
  6. customPurify by silica gel chromatography (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c3345879c2334a04a2e5143786208055
Source dataset
uspto-grants-1993_10
Patent number
US05252601

Linked notes

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