Diisopropylethylamine → (S,E)-2-(3-(2-(tert-butoxycarbonylamino)-7-methoxy-7-oxohept-5-enamido)-2-oxopyridin-1(2H)-yl)acetic acid

HRID 58323

반응식

HRID 58323 반응식
C([O:5][C:6](=[O:35])[CH2:7][N:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][C:15](=[O:33])[C@@H:16]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:17][CH2:18]/[CH:19]=[CH:20]/[C:21]([O:23][CH3:24])=[O:22])[C:9]1=[O:34])(C)(C)C.CCN(C(C)C)C(C)C.C(ON1C(=O)CCC1=O)(OC(C)(C)C)=O>ClCCl.FC(F)(F)C(O)=O.CN(C=O)C>[C:29]([O:28][C:26]([NH:25][C@@H:16]([CH2:17][CH2:18]/[CH:19]=[CH:20]/[C:21]([O:23][CH3:24])=[O:22])[C:15]([NH:14][C:10]1[C:9](=[O:34])[N:8]([CH2:7][C:6]([OH:35])=[O:5])[CH:13]=[CH:12][CH:11]=1)=[O:33])=[O:27])([CH3:32])([CH3:31])[CH3:30]

참가 물질

7

반응물 3

HCID 81531Diisopropylethylamine2회HCID 83168Carbonic acid, 1,1-dimethylethyl 2,5-dioxo-1-pyrrolidinyl esterHCID 118104203(S,E)-Methyl 7-(1-(2-tert-butoxy-2-oxoethyl)-2-oxo-1,2-dihydropyridin-3-yl-amino)-6-(tert-butoxycarbonylamino)-7-oxohept-2-enoate

생성물 1

HCID 89925798(S,E)-2-(3-(2-(tert-butoxycarbonylamino)-7-methoxy-7-oxohept-5-enamido)-2-oxopyridin-1(2H)-yl)acetic acid

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 6422Trifluoroacetic acid용매

실험 절차

590 mg of (S,E)-methyl 7-(1-(2-tert-butoxy-2-oxoethyl)-2-oxo-1,2-dihydropyridin-3-yl-amino)-6-(tert-butoxycarbonylamino)-7-oxohept-2-enoate (ZED1209, 1.20 mmol) are dissolved in 10 mL of dichloromethane and to this solution 10 mL of trifluoroacetic acid is added. It is stirred at RT for 1 h. The solvent is removed in vacuo and the residue is dried under high vacuum. The obtained oil is further reacted without purification. The oil is taken up in 15 mL of DMF and treated with 173 μL of DIPEA. By successive addition of DIPEA the pH value is adjusted to ca. 7. To this solution, 285 mg of Boc-OSu (1.1 eq) are added and stirred at RT overnight. The solvent is removed in vacuo and the residue is purified by preparative HPLC (30% ACN in water, 8 mL/min, gradient 1% pro min).

후처리

  1. additionis added
  2. customThe solvent is removed in vacuo
  3. customthe residue is dried under high vacuum
  4. customThe obtained oil is further reacted without purification
  5. stirringstirred at RT overnight
  6. customThe solvent is removed in vacuo
  7. customthe residue is purified by preparative HPLC (30% ACN in water, 8 mL/min, gradient 1% pro min)

출처 및 근거

ORD 기록
ord-743b7f1dad3644efb3a46de49b7848db
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434763B2

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