Hydrochloric Acid → Boc-homophenylalaninal

HRID 1595145

反応式

HRID 1595145 の反応式
N1(C(N[C@H](C(O)=O)[CH2:11][C:12]2[CH:17]=CC=C[CH:13]=2)=O)CCOCC1.CN1CC[O:25]CC1.Cl[C:29]([O:31]CC(C)C)=[O:30].Cl.[NH2:37][C@@H:38]([CH2:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[CH:39]=CC(OCC)=O.Cl>C1COCC1.CN(C=O)C>[C:29]([NH:37][C@H:38]([CH:39]=[O:25])[CH2:46][CH2:47][C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1)([O:31][C:12]([CH3:11])([CH3:13])[CH3:17])=[O:30]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 79724-Methylmorpholine2 回HCID 62365Isobutyl chloroformateHCID 664657CP 84364HCID 86754733ethyl (S)-4-amino-6-phenyl-2-hexenoate hydrochloride

生成物 1

HCID 10264740Boc-homophenylalaninal収率 80%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Morpholinecarbonylphenylalanine (2.74 g, 9.82 mmol, prepared according to the method described in Esser, R. et.al., Arthritis & Rheumatism (1994), 0000) was dissolved in THF (50 mL) at −10° C. 4-methylmorpholine (1.08 mL, 9.82 mmol) was added, followed by isobutyl chloroformate (1.27 mL, 9.82 mmol). The mixed anhydride was stirred for 10 minutes, whereupon a solution of ethyl (S)-4-amino-6-phenyl-2-hexenoate hydrochloride from the previous step in DMF (10 mL) was added, followed by 4-methylmorpholine (1.08 mL, 9.82 mmol). The mixture was stirred for 1 hour. 1M HCl (50 mL) was added. The product was extracted with ethyl acetate (100 mL), washed with saturated aqueous NaHCO3 (50 mL), dried over MgSO4 and decolorizing charcoal (DARCO), filtered, and evaporated to dryness, giving 3.80 g (80% yield from Boc-homophenylalaninal).

後処理

  1. additionwas added
  2. extractionThe product was extracted with ethyl acetate (100 mL)
  3. washwashed with saturated aqueous NaHCO3 (50 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness

出典と根拠

ORDレコード
ord-2223d055049e41c1a37c87f1d8e69ad7
出典データセット
uspto-grants-2001_09
特許番号
US06287840B1

関連ノート

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