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

HRID 58323

反応式

HRID 58323 の反応式
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]

参加物

7

反応物 3

HCID 81531Diisopropylethylamine2 回HCID 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒HCID 6422Trifluoroacetic acid溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-743b7f1dad3644efb3a46de49b7848db
出典データセット
uspto-grants-2016_09
特許番号
US09434763B2

関連ノート

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