HCID 57011577, compound → (2S,4R)-2-(tert-butoxycarbonyl)amino-4-(benzyloxymethyl)-5-methyl-hexanoic acid methyl ester

HRID 1684749Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:22][C@H:23]([CH2:27][O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH:24]([CH3:26])[CH3:25])[C@@H:10]([OH:21])CC(=C)C(NCCCC)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:36]([O:40]C(N[C@@H](C[C@H](COCC1C=CC=CC=1)C(C)C)[C@H](O)CC(=C)C(NCCCC)=O)=O)(C)(C)C>>[CH3:36][O:40][C:10](=[O:21])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[CH2:22][C@@H:23]([CH2:27][O:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[CH:24]([CH3:25])[CH3:26]

Participants

Reactant 2

HCID 57011577HCID 57011577, compound

HCID 57309556HCID 57309556, compound

Product 1

HCID 69646278(2S,4R)-2-(tert-butoxycarbonyl)amino-4-(benzyloxymethyl)-5-methyl-hexanoic acid methyl ester

Procedure

(2S,3S,5R)-2-[3-(tert-Butoxycarbonyl)amino-5-(benzyloxymethyl)-2-hydroxy-6-methylheptyl]-N-(butyl)acrylamide (A) and (2R,3S,5R)-2-[3-(tert-butoxycarbonyl)amino-5-(benzyloxymethyl)-2-hydroxy-6-methylheptyl]-N-(butyl)acrylamide (B): In a manner analogous to that described in Example 1g), there is obtained first, by reduction of (2S,4R)-2-(tert-butoxycarbonyl)amino-4-(benzyloxymethyl)-5-methyl-hexanoic acid methyl ester (8.0 g), dissolved in anhydrous toluene (120 ml), with a 1.2M diisobutylaluminium hydride solution in toluene (34.9 ml), (2S,4R)-2-(tert-butoxycarbonyl)amino-4-(benzyloxymethyl)-5-methyl-hexanal in the form of a pale-yellow oil (Rf (N)=0.6). The crude aldehyde is reacted in a manner analogous to that described in Example 1g) without being purified further. The crude product (14.8 g) obtained after aqueous working-up is chromatographed over 1.0 kg of silica gel using an eluant gradient from B to E, with separation of the two (2S,3S,5R)- and (2R,3S,5R)-diastereoisomers. There are obtained title compound A (2.52 g, 24%) in the form of a light-yellow oil, Rf (E)=0.55, HPLC Rt =19.8 min, MS(FAB) m/e 491 (M+ +1), and title compound B (3.76 g, 35%) in the form of a light-yellow oil, Rf (E)=0.42, HPLC Rt =19.6 min. MS(FAB) m/e 491 (M+ +1).

Sources & evidence

ORD record: ord-1db4d9a56e2648be9919f651213f5cc9
Source dataset: uspto-grants-1997_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05641778

Reaction notes

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