4-Methylmorpholine → (R)-3-mercapto-2-[(S)-2-methyl-3-trityloxy-propionylamino]-propionic acid methyl ester

HRID 234211노트

반응식

HRID 234211 반응식
[C:1]([O:20][C@@H](C)C(O)=O)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:27][O:28][C:29](=[O:34])[C@H:30]([CH2:32][SH:33])[NH2:31].Cl.CN(C)[CH2:38][CH2:39][CH2:40]N=C=NCC.CN1CC[O:51][CH2:50]C1>C(#N)C>[CH3:27][O:28][C:29](=[O:34])[C@@H:30]([NH:31][C:50](=[O:51])[C@@H:39]([CH3:38])[CH2:40][O:20][C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH2:32][SH:33]

참가 물질

6

반응물 4

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2733208L-Cysteine, methyl ester, hydrochlorideHCID 54161083(S)-2-trityloxypropionic acid

생성물 1

HCID 54008528(R)-3-mercapto-2-[(S)-2-methyl-3-trityloxy-propionylamino]-propionic acid methyl ester수율 16.5%

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

To a suspension of 9.97 g of (S)-2-trityloxy-propionic acid, 5.60 g of L-cysteine methyl ester hydrochloride and 6.6 g of N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride in 50 ml acetonitrile was added over 10 min a solution of 6.9 g of 4-methyl-morpholine in 50 ml of acetonitrile. The mixture was stirred at room temperature for 3 h and then partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel using ethyl acetate/hexane (1:2, v/v) as eluent to yield 2.30 g of (R)-3-mercapto-2-[(S)-2-methyl-3-trityloxy-propionylamino]-propionic acid methyl ester as amorphous solid. 1H-NMR (250 MHz,DMSO-d6): δ0.88(d,J=10 Hz,3H); 2.42(t,J=15 Hz, 1H); 2.78 (dd,J=10 Hz and 15 Hz,2H); 3.66(s,3H); 4.01(q,J=10 Hz, 1H); 4.20-4.30(m, 1H); 7.25-7.50(m, 16H); 7.82(d,J=16 Hz,1H) ppm.

후처리

  1. custompartitioned between water and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on silica gel

출처 및 근거

ORD 기록
ord-e0c84cc91f1d439183e58be7b2c7be11
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05594135

반응 노트

불러오는 중…