Acetic Acid → HCID 86587960, compound

HRID 25745

Reaction equation

HRID 25745 reaction equation
[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]

Participants

7

Reactant 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

Product 1

HCID 86587960HCID 86587960, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-fa57dbcf2d694c799b7d894ffe6fbb26
Source dataset
uspto-grants-2005_02
Patent number
US06858591B2

Linked notes

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