Acetic Acid → HCID 86587960, 화합물

HRID 25745

반응식

HRID 25745 반응식
[C:1](OC(C)CC(=O)NCCC=O)(=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[C:27]([O-:31])(=O)[CH2:28]C.[Si]([O:39][C@H:40]1[C@H:44]([N:45]2[CH:50]=[CH:49][C:48](=[O:51])[N:47](CC3C=CC(OC)=CC=3)[C:46]2=[O:61])[O:43][CH:42]([C@H:62]([OH:89])[C@@H:63]([C:86]([OH:88])=[O:87])[NH:64][CH2:65][CH2:66][CH2:67][NH:68][C:69](=[O:85])[C@H:70]([C@@H:82]([OH:84])[CH3:83])[NH:71][C:72](=[O:81])[O:73][CH2:74][C:75]2[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=2)[C@H:41]1[OH:90])(C(C)(C)C)(C)C.[C:91]([OH:94])(=O)[CH3:92].[C:95](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:96].[Na+]>O1CCCC1>[C:91]([O:90][C@H:41]1[C@@H:40]([O:39][C:27](=[O:31])[CH3:28])[C@H:44]([N:45]2[CH:50]=[CH:49][C:48](=[O:51])[NH:47][C:46]2=[O:61])[O:43][C@@H:42]1[C@H:62]([OH:89])[CH:63]([C:86]([O:88][CH2:95][CH3:96])=[O:87])[NH:64][CH2:65][CH2:66][CH2:67][NH:68][C:69](=[O:85])[C@H:70]([C@@H:82]([O:84][C:1](=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH3:83])[NH:71][C:72](=[O:81])[O:73][CH2:74][C:75]1[CH:76]=[CH:77][CH:78]=[CH:79][CH:80]=1)(=[O:94])[CH3:92]

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 104745Propionate ionHCID 5049666Sodium triacetoxyborohydrideHCID 69752535(5S,12S)-12-[(R)-[(3R,4R,5R)-4-{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-5-(3-(4-methoxybenzyl)-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)tetrahydro-2-furanyl](hydroxy)methyl]-5-[(1S)-1-hydroxyethyl]-3,6-dioxo-1-phenyl-2-oxa-4,7,11-triazatridecan-13-oic acidHCID 865879611-Methyl-3-oxo-3-[(3-oxopropyl)amino]propyl myristate

생성물 1

HCID 86587960HCID 86587960, 화합물수율 22%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

By using an analogous procedure to that described for Example 56, a solution of (1S,2S)-2-1[(benzyloxy)carbonyl]amino}-1-methyl-3-oxo-3-[(3-oxopropyl)amino]propyl myristate (250 mg, 0.483 mmol, obtained from Reference Example 48) and the hydrogen chloride salt mixture of ethyl (2R,3R)-3-(acetyloxy)-2-dihydro-1(2H)-pyrimidinyl)tetrahydro-2-furanyl]propanoate and ethyl (2R,3R)-3-(acetyloxy)-2-{[(benzyloxy)carbonyl]amino}-3-[(2R,3R,4R,5S)-3,4-bis(acetyloxy)-5-(2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)tetrahydro-2-furanyl]propanoate (207 mg, 0.483 mmol, obtained from Reference Example 46), acetic acid (0.028 ml, 0.483 mmol) and sodium triacetoxyborohydride (205 mg, 0.97 mmol) in anhydrous tetrahydrofuran (4 ml) was stirred at room temperature under a nitrogen atmosphere for 16 hours. The product was chromatographed (flash column, silica gel, 75% ethyl acetate in hexane) to provide ethyl (5S)-12-[(R)-[(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2 h)-yl)tetrahydrofuran-2-yl](hydroxy)methyl]-3,6-dioxo-1-phenyl-5-[(1S)-1-(tetradecanoyloxy)ethyl]-2-oxa-4,7,11-triazatridecan-13-oate (100 mg, 22%) as a white amorphous solid.

후처리

  1. customThe product was chromatographed (flash column, silica gel, 75% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-fa57dbcf2d694c799b7d894ffe6fbb26
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858591B2

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