三乙胺 → Boc-Tyr(OBn)-Ser(OBn)-CO2Me

HRID 355521

反应方程式

HRID 355521 反应方程式
[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

参与物

7

反应物 5

HCID 8471三乙胺HCID 10868N,N'-二环己基碳二亚胺HCID 98763Boc-O-苄基-L-酪氨酸HCID 27960291-羟基苯并三唑一水物HCID 131720920Ser(OBn)-CO2Me.TFA

产物 1

HCID 131720919Boc-Tyr(OBn)-Ser(OBn)-CO2Me收率 73%

试剂、催化剂与溶剂 1

HCID 8857乙酸乙酯溶剂2 次

实验过程

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.

后处理

  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

来源与证据

ORD记录
ord-b912eaba23384d21b5d4e1751cf41837
来源数据集
uspto-grants-1998_11
专利号
US05830868

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