Triethylamine → N-BOC-m-Benzoyl-L-Phenylalanine

HRID 34686

반응식

HRID 34686 반응식
[C:1]([C:9]1[CH:10]=[C:11]([CH:18]=[CH:19][CH:20]=1)[CH2:12][C@@H:13]([C:15]([OH:17])=[O:16])[NH2:14])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:28][C:29]([O:32][C:33](ON=C(C1C=CC=CC=1)C#N)=[O:34])([CH3:31])[CH3:30]>O.CC(C)=O>[C:33]([NH:14][C@H:13]([C:15]([OH:17])=[O:16])[CH2:12][C:11]1[CH:18]=[CH:19][CH:20]=[C:9]([C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:10]=1)([O:32][C:29]([CH3:31])([CH3:30])[CH3:28])=[O:34]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrileHCID 14233367m-benzoyl-L-phenylalanine

생성물 1

HCID 14233370N-BOC-m-Benzoyl-L-Phenylalanine

시약·촉매·용매 2

HCID 180Acetone용매HCID 962Water용매

실험 절차

A suspension of 2.175 g of m-benzoyl-L-phenylalanine in 25 ml of water and 1.15 g of triethylamine was treated with 3.35 g of BOC-ON in 40 ml of acetone. After 3 h, acetone was removed and the aqueous residue was extracted three times with ether (discarded). The aqueous solution was acidified to pH 2 with 1N hydrochloric acid and extracted with ethyl acetate. The extract was dried (MgSO4) and stripped. The residue was triturated for 7 days with petroleum ether. The waxy insoluble solid was triturated for 14 days with an additional portion of petroleum ether and finally for 7 days with a third portion. The resulting white solid weighed 1.786 g after vacuum drying, [α]D25 +22.2±0.9°, C=0.86 g/100 ml ethanol. Anal.: Calcd. for C21H23NO5 :C, 68.28; H, 6.28; N, 3.79. Found: C, 68.01; H, 6.49; N, 3.68.

후처리

  1. customacetone was removed
  2. extractionthe aqueous residue was extracted three times with ether (discarded)
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extract was dried (MgSO4)
  5. customThe residue was triturated for 7 days with petroleum ether
  6. customThe waxy insoluble solid was triturated for 14 days with an additional portion of petroleum ether and finally for 7 days with a third portion
  7. customdrying

출처 및 근거

ORD 기록
ord-0315a666c64b43fd98a8efb3ebeb32e5
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04762881

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