Acetic Acid → HCID 86587960、化合物

HRID 25745

反応式

HRID 25745 の反応式
[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]

参加物

7

反応物 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

生成物 1

HCID 86587960HCID 86587960、化合物収率 22%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-fa57dbcf2d694c799b7d894ffe6fbb26
出典データセット
uspto-grants-2005_02
特許番号
US06858591B2

関連ノート

読み込み中…