Piperidine → HCID 10191296, compound

HRID 25727Notes

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:79])[C@H:40]([NH:48][C:49](=[O:78])[CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][NH:60]C(OCC1C2C=CC=CC=2C2C1=CC=CC=2)=O)[C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1CCCCC1>>[NH2:60][CH2:59][CH2:58][CH2:57][CH2:56][CH2:55][CH2:54][CH2:53][CH2:52][CH2:51][CH2:50][C:49]([NH:48][C@@H:40]([C@H:39]([CH:10]1[C@@H:9]([O:8][Si:1]([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2])[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:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=3)[C:23]2=[O:38])[O:11]1)[OH:79])[C:41]([O:43][C:44]([CH3:45])([CH3:46])[CH3:47])=[O:42])=[O:78]

Participants

Reactant 2

HCID 8082Piperidine

HCID 59985741HCID 59985741, compound

Product 1

HCID 10191296HCID 10191296, compoundYield 65%

Procedure

By using an analogous procedure to that described for Reference Example 32, tert-butyl (2S,3R)-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]-2-[(11-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}undecanoyl)amino]-3-hydroxypropanoate (73 mg, 0.065 mmol, obtained from Example 22) was stirred with piperidine (1.5 ml) for 1 hour under nitrogen at room temperature. The product was purified by chromatography (flash column, silica gel, 50-60% methanol in methylene chloride) to provide tert-butyl (2S,3R)-2-[(11-aminoundecanoyl)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 (38 mg, 65%) as a white solid.

Workup

customThe product was purified by chromatography (flash column, silica gel, 50-60% methanol in methylene chloride)

Sources & evidence

ORD record: ord-bdc95a0cba6b4d52a9c80fa9a1d44a64
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06858591B2

Reaction notes

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