Sodium triacetoxyborohydride → HCID 59065931, compound

HRID 25718Notes

Reaction equation

HRID 25718 reaction equation
[CH2:1]([C@H:8]([NH:16][C:17](=[O:26])[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:9](=[O:15])[NH:10][CH2:11][CH2:12][CH:13]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:27][C@@H:28]([C@H:36]([C@@H:38]1[C@@H:42]([O:43][Si:44]([C:47]([CH3:50])([CH3:49])[CH3:48])([CH3:46])[CH3:45])[C@@H:41]([O:51][Si:52]([C:55]([CH3:58])([CH3:57])[CH3:56])([CH3:54])[CH3:53])[C@H:40]([N:59]2[CH:64]=[CH:63][C:62](=[O:65])[N:61]([CH2:66][C:67]3[CH:72]=[CH:71][C:70]([O:73][CH3:74])=[CH:69][CH:68]=3)[C:60]2=[O:75])[O:39]1)[OH:37])[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C.O1CCCC1>[CH2:1]([C@@H:8]([C:9](=[O:15])[NH:10][CH2:11][CH2:12][CH2:13][NH:27][C@@H:28]([C@H:36]([CH:38]1[C@@H:42]([O:43][Si:44]([C:47]([CH3:48])([CH3:49])[CH3:50])([CH3:46])[CH3:45])[C@@H:41]([O:51][Si:52]([C:55]([CH3:58])([CH3:57])[CH3:56])([CH3:53])[CH3:54])[C@H:40]([N:59]2[CH:64]=[CH:63][C:62](=[O:65])[N:61]([CH2:66][C:67]3[CH:72]=[CH:71][C:70]([O:73][CH3:74])=[CH:69][CH:68]=3)[C:60]2=[O:75])[O:39]1)[OH:37])[C:29]([O:31][C:32]([CH3:34])([CH3:33])[CH3:35])=[O:30])[NH:16][C:17](=[O:26])[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 12137063tert-butyl (2S,3R)-2-amino-3-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl-(dimethyl)silyl]oxy}-5-(3-(4-methoxybenzyl)-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)-tetrahydro-2-furanyl]-3-hydroxy-propanoateHCID 59065893benzyl (1S)-1-benzyl-2-oxo-2-[(3-oxopropyl)amino]ethylcarbamate

Product 1

HCID 59065931HCID 59065931, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 8028TetrahydrofuranSolvent

Procedure

By using an analogous procedure to that described for Example 1, a solution of benzyl (1S)-1-benzyl-2-oxo-2-[(3-oxopropyl)amino]ethylcarbamate (61 mg, 0.173 mmol, obtained from Reference Example 22), tert-butyl (2S,3R)-2-amino-3-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl-(dimethyl)silyl]oxy}-5-(3-(4-methoxybenzyl)-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)-tetrahydro-2-furanyl]-3-hydroxypropanoate (100 mg, 0.139 mmol, obtained from Reference Example 6), acetic acid (1 drop), and sodium triacetoxyborohydride (59 mg, 0.277 mmol) in anhydrous tetrahydrofuran (4 ml) was stirred at room temperature under nitrogen for 5 hours. The product was purified by chromatography (flash column, silica gel, 2.5% methanol in methylene chloride) to provide tert-butyl (5S,12S)-5-benzyl-12-[(R)-[(3R,4R,5R)-3,4-bis{[tertbutyl(dimethyl)silyl]oxy}-5-(3-(4-methoxybenzyl)-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)tetrahydro-2-furanyl](hydroxy)methyl]-3,6-dioxo-1-phenyl-2-oxa-4,7,11-triazatridecan-13-oate (31 mg, 21%) as a white solid.

Workup

  1. customThe product was purified by chromatography (flash column, silica gel, 2.5% methanol in methylene chloride)

Sources & evidence

ORD record
ord-10428b476c594334bdba798ae55264e4
Source dataset
uspto-grants-2005_02
Patent number
US06858591B2

Reaction notes

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