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

HRID 1656049

반응식

HRID 1656049 반응식
[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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-c3345879c2334a04a2e5143786208055
출처 데이터셋
uspto-grants-1993_10
특허 번호
US05252601

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