tert-butyl (21S)-21-[(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]-11-(9H-fluoren-9-yl)-3,15-dioxo-2-oxa-4,16,20-triazadocosan-22-oate → HCID 10191481, compound

HRID 25729Notes

Reaction equation

HRID 25729 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])[N:24]([CH2:29][C:30]3[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=3)[C:23]2=[O:38])[O:11][CH:10]1[C@H:39]([OH:83])[C@@H:40]([C:76]([O:78][C:79]([CH3:82])([CH3:81])[CH3:80])=[O:77])[NH:41][CH2:42][CH2:43][CH2:44][NH:45][C:46](=[O:75])[CH2:47][CH2:48][CH2:49][CH:50](C1C2C=CC=CC=2C2C1=CC=CC=2)[CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][NH:57]C(=O)OC)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>N1CCCCC1>[NH2:57][CH2:56][CH2:55][CH2:54][CH2:53][CH2:52][CH2:51][CH2:50][CH2:49][CH2:48][CH2:47][C:46]([NH:45][CH2:44][CH2:43][CH2:42][NH:41][C@@H:40]([C@H:39]([CH:10]1[C@@H:9]([O:8][Si:1]([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:2])[CH3:3])[C@@H:13]([O:14][Si:15]([C:18]([CH3:19])([CH3:20])[CH3:21])([CH3:17])[CH3:16])[C@H:12]([N:22]2[CH:27]=[CH:26][C:25](=[O:28])[N:24]([CH2:29][C:30]3[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=3)[C:23]2=[O:38])[O:11]1)[OH:83])[C:76]([O:78][C:79]([CH3:80])([CH3:81])[CH3:82])=[O:77])=[O:75]

Participants

3

Reactant 1

HCID 86587946tert-butyl (21S)-21-[(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]-11-(9H-fluoren-9-yl)-3,15-dioxo-2-oxa-4,16,20-triazadocosan-22-oate

Product 1

HCID 10191481HCID 10191481, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8082PiperidineSolvent

Procedure

By using an analogous procedure to that described for Reference Example 32, a solution of tert-butyl (21S)-21-[(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]-11-(9H-fluoren-9-yl)-3,15-dioxo-2-oxa-4,16,20-triazadocosan-22-oate (106 mg, 0.09 mmol, obtained from Example 24) in piperidine (3 ml) was stirred for 1.5 hours under nitrogen at room temperature. The product was purified by chromatography (flash column, silica gel, 60-100% methanol in methylene chloride) to provide tert-butyl (2S,3R)-2-({3-[(11-aminoundecanoyl)amino]propyl}amino)-3-[(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 (44 mg, 51%) as a white solid.

Workup

  1. customThe product was purified by chromatography (flash column, silica gel, 60-100% methanol in methylene chloride)

Sources & evidence

ORD record
ord-c8a3f1707a11479f90cdd6a6fe8a1695
Source dataset
uspto-grants-2005_02
Patent number
US06858591B2

Reaction notes

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