HCID 59065931, compound → HCID 59065919, compound

HRID 25719Notes

Reaction equation

HRID 25719 reaction equation
[CH2:1]([C@@H:8]([C:20](=[O:74])[NH:21][CH2:22][CH2:23][CH2:24][NH:25][C@@H:26]([C@H:34]([CH:36]1[C@@H:40]([O:41][Si:42]([C:45]([CH3:48])([CH3:47])[CH3:46])([CH3:44])[CH3:43])[C@@H:39]([O:49][Si:50]([C:53]([CH3:56])([CH3:55])[CH3:54])([CH3:52])[CH3:51])[C@H:38]([N:57]2[CH:62]=[CH:61][C:60](=[O:63])[N:59]([CH2:64][C:65]3[CH:70]=[CH:69][C:68]([O:71][CH3:72])=[CH:67][CH:66]=3)[C:58]2=[O:73])[O:37]1)[OH:35])[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[NH:9]C(=O)OCC1C=CC=CC=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[Pd]>[NH2:9][C@@H:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:20]([NH:21][CH2:22][CH2:23][CH2:24][NH:25][C@@H:26]([C@H:34]([CH:36]1[C@@H:40]([O:41][Si:42]([C:45]([CH3:46])([CH3:47])[CH3:48])([CH3:43])[CH3:44])[C@@H:39]([O:49][Si:50]([C:53]([CH3:54])([CH3:55])[CH3:56])([CH3:52])[CH3:51])[C@H:38]([N:57]2[CH:62]=[CH:61][C:60](=[O:63])[N:59]([CH2:64][C:65]3[CH:70]=[CH:69][C:68]([O:71][CH3:72])=[CH:67][CH:66]=3)[C:58]2=[O:73])[O:37]1)[OH:35])[C:27]([O:29][C:30]([CH3:32])([CH3:33])[CH3:31])=[O:28])=[O:74]

Participants

4

Reactant 1

HCID 59065931HCID 59065931, compound

Product 1

HCID 59065919HCID 59065919, compoundYield 70.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

By using an analogous procedure to that described for Example 2, 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 (Example 12) (49 mg, 0.046 mmol) was hydrogenated in methanol (1.5 ml) using 10% palladium on carbon (12 mg) to provide tert-butyl (2S,3R)-2-[(3-{[(2S)-2-amino-3-phenylpropanoyl]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 (30 mg, 70%) as a white amorphous solid.

Sources & evidence

ORD record
ord-c0d9738ce0a04465b864c65c9fb5b2d2
Source dataset
uspto-grants-2005_02
Patent number
US06858591B2

Reaction notes

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