Tetrahydrofuran → HCID 59065917, compound

HRID 25720Notes

Reaction equation

HRID 25720 reaction equation
[Si:1]([O:8][C@H:9]1[C@@H:13]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[C@H:12]([N:22]2[CH:27]=[CH:26][C:25](=[O:28])[NH:24][C:23]2=[O:29])[O:11][CH:10]1[C@H:30]([OH:62])[C@@H:31]([C:55]([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:56])[NH:32][CH2:33][CH2:34][CH2:35][NH:36][C:37](=[O:54])[C@H:38](CC(C)C)[NH:39][C:40](=[O:49])[O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C[C@H](NC(=O)O[CH2:75][C:76]1[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=1)C(=O)NCCC=O.[C:83](O[BH-](OC(=O)C)OC(=O)C)(=[O:85])C.[Na+].O1CCC[CH2:98]1>C(O)(=O)C>[Si:1]([O:8][C@H:9]1[C@@H:13]([O:14][Si:15]([C:18]([CH3:21])([CH3:19])[CH3:20])([CH3:17])[CH3:16])[C@H:12]([N:22]2[CH:27]=[CH:26][C:25](=[O:28])[N:24]([CH2:75][C:76]3[CH:77]=[CH:78][C:79]([O:85][CH3:83])=[CH:80][CH:81]=3)[C:23]2=[O:29])[O:11][CH:10]1[C@H:30]([OH:62])[C@@H:31]([C:55]([O:57][C:58]([CH3:60])([CH3:61])[CH3:59])=[O:56])[NH:32][CH2:33][CH2:34][CH2:35][NH:36][C:37](=[O:54])[C@H:38]([CH3:98])[NH:39][C:40](=[O:49])[O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 5049666Sodium triacetoxyborohydrideHCID 59065906benzyl (1S)-1-methyl-2-oxo-2-[(3-oxopropyl)amino]ethylcarbamateHCID 59065937HCID 59065937, compound

Product 1

HCID 59065917HCID 59065917, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidCatalyst

Procedure

By using an analogous procedure to that described for Example 1, a solution of tert-(4-methoxybenzyl)-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)-tetrahydro-2-furanyl]-3-hydroxypropanoate (80 mg, 0.111 mmol, obtained from Reference Example 6), benzyl (1S)-1-methyl-2-oxo-2-[(3-oxopropyl)amino]ethylcarbamate (39 mg, 0.139 mmol, obtained from Reference Example 20), acetic acid (1 drop), and sodium triacetoxyborohydride (47 mg, 0.222 mmol) in anhydrous tetrahydrofuran (4 ml) was stirred at room temperature under nitrogen for 3 hours. The product was purified by chromatography (flash column, silica gel, 5% methanol in methylene chloride) to provide tert-butyl (5S,12S)-12-[(R)-[(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](hydroxy)methyl]-5-methyl-3,6-dioxo-1-phenyl-2-oxa-4,7,11-triazatridecan-13-oate (43 mg, 39%) as a white amorphous solid.

Workup

  1. customThe product was purified by chromatography (flash column, silica gel, 5% methanol in methylene chloride)

Sources & evidence

ORD record
ord-012974ea7b924d48b288baf598a885fc
Source dataset
uspto-grants-2005_02
Patent number
US06858591B2

Reaction notes

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