Triethylamine → Boc-Tyr(OBn)-Ser(OBn)-CO2Me

HRID 355521

반응식

HRID 355521 반응식
[NH:1]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@H:2]([C:18](O)=[O:19])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1.C1C=C2N=NN(O)C2=CC=1.O.C1CCC(N=C=NC2CCCCC2)CC1.[NH2:54][C@H:55]([C:65]([C:67]([O:69][CH3:70])=[O:68])=[O:66])[CH2:56][O:57][CH2:58][C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1.FC(C(O)=O)(F)F.CCN(CC)CC>CCOC(C)=O>[NH:1]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@H:2]([C:18]([NH:54][C@H:55]([C:65]([C:67]([O:69][CH3:70])=[O:68])=[O:66])[CH2:56][O:57][CH2:58][C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)=[O:19])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 98763O-benzyl-N-((tert-butoxy)carbonyl)-L-tyrosineHCID 27960291-Hydroxybenzotriazole hydrateHCID 131720920Ser(OBn)-CO2Me.TFA

생성물 1

HCID 131720919Boc-Tyr(OBn)-Ser(OBn)-CO2Me수율 73%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매2회

실험 절차

To a solution of Boc-Tyr(OBn) (1.88 g, 6.50 mmol) in EtOAc (30 mL) at 0° C. was added HOBT hydrate (1.19 g, 7.80 mmol) followed by DCC (1.61 g, 7.80 mmol). A solution of Ser(OBn)-CO2Me.TFA (2.1 g, 6.50 mmol) in EtOAc (20 mL) was added followed by Et3N (1.09 mL, 7.80 mmol). The mixture was allowed to warm to room temperature and stirred overnight. The mixture was filtered, diluted with EtOAc, and washed twice with saturated aqueous NaHCO3, brine, dried over MgSO4, and concentrated. Flash chromatography (40% EtOAc/hexane) gave 2.67 g (73%) of the title compound as a white solid, mp 81°-84° C.

후처리

  1. filtrationThe mixture was filtered
  2. additiondiluted with EtOAc
  3. washwashed twice with saturated aqueous NaHCO3, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-b912eaba23384d21b5d4e1751cf41837
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05830868

연결된 노트

불러오는 중…