Cytidine → N-Hexadecanoylcytidine

HRID 335373

반응식

HRID 335373 반응식
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([NH:18][C:19]1[CH:25]=[CH:24][N:23]([C@@H:26]2[O:30][C@H:29]([CH2:31][OH:32])[C@@H:28]([OH:33])[C@@H:27]2C#N)[C:21](=[O:22])[N:20]=1)=[O:17].[C@@H]1(N2C=CC(N)=NC2=O)O[C@H](CO)[C@@H](O)[C@H]1[OH:38].C(OC(=O)CCCCCCCCCCCCCCC)(=O)CCCCCCCCCCCCCCC>CN(C=O)C>[C:16]([NH:18][C:19]1[CH:25]=[CH:24][N:23]([C@@H:26]2[O:30][C@H:29]([CH2:31][OH:32])[C@@H:28]([OH:33])[C@H:27]2[OH:38])[C:21](=[O:22])[N:20]=1)(=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1]

참가 물질

5

반응물 3

HCID 6175CytidineHCID 69339Palmitic anhydrideHCID 153970Sapacitabine

생성물 1

HCID 22879539N-Hexadecanoylcytidine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

The preparation of CYC682 described in EP 536936 (see Scheme 1 below) involves reacting cytidine [1] with palmitic anhydride in DMF to form N4-palmitoylcytidine [2] and subsequently protecting with 1,3-dichloro-1,1,4,4-tetraisopropyldisiloxane (CIPS) to form intermediate [3]. Oxidation of [3] with pyridinium dichromate/acetic anhydride in dichloromethane produces intermediate ketone [4], which is then reacted with sodium cyanide and sodium dihydrogen phosphate dihydrate in ethyl acetate to form the cyanohydrin [5]. Intermediate [5] is then reacted with N,N-dimethylaminopyridine, phenoxythiocarbonyl chloride and triethylamine to form intermediate [6], which is subsequently reacted with AIBN and tributyltin hydride in toluene to give intermediate [7]. Deprotection of [7] with acetic acid and tetrabutylammonium fluoride in THF yields the desired product, CYC682.

출처 및 근거

ORD 기록
ord-bd91e273fcae44968a3f4283f4c7f41c
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08884001B2

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