(2s)-2-Aminopentane-1,5-diol → (3S,6S)-3-(3-Hydroxy-propyl)-6-methyl-5-oxo-hexahydro-oxazolo[3,2-a]pyrazine-7-carboxylic acid benzyl ester

HRID 1261843Notes

Reaction equation

HRID 1261843 reaction equation
COC(=O)[C@@H](N(C(OCC1C=CC=CC=1)=O)CC=O)C.N[C@@H](CCCO)CO.[CH2:29]([O:36][C:37]([N:39]1[CH2:51][CH:43]2[O:44][CH2:45][CH2:46][CH2:47][C@@H:48]([CH2:49][OH:50])[N:42]2[C:41](=[O:52])[C@@H:40]1[CH3:53])=[O:38])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[CH2:29]([O:36][C:37]([N:39]1[C@@H:40]([CH3:53])[C:41](=[O:52])[N:42]2[C@@H:48]([CH2:47][CH2:46][CH2:45][OH:44])[CH2:49][O:50][CH:43]2[CH2:51]1)=[O:38])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

4

Reactant 3

HCID 11829415(2s)-2-Aminopentane-1,5-diolHCID 67093093(3S,5S)-5-hydroxymethyl-3-methyl-4-oxo-octahydro-9-oxa-2,4a-diaza-benzocycloheptene-2-carboxylic acid benzyl esterHCID 86638111(S)-2-[Benzyloxycarbonyl-(2-oxo-ethyl)-amino]-propionic acid methyl ester2×

Product 1

HCID 67092675(3S,6S)-3-(3-Hydroxy-propyl)-6-methyl-5-oxo-hexahydro-oxazolo[3,2-a]pyrazine-7-carboxylic acid benzyl ester

Procedure

Condensation of (S)-2-[benzyloxycarbonyl-(2-oxo-ethyl)-amino]-propionic acid methyl ester (intermediate 1) with (S)-2-amino-pentane-1,5-diol in analogy with examples 1/2F produced a nearly statistical mixture of the title compound [light yellow gum, MS: 349.3 (M+H)+] and (3S,5S)-5-hydroxymethyl-3-methyl-4-oxo-octahydro-9-oxa-2,4a-diaza-benzocycloheptene-2-carboxylic acid benzyl ester [light yellow gum, MS:349.3 (M+H)|], which were separated by column chromatography (SiO2; DCM→DCM/MeOH/25% aq. ammonia solution 90:10:0.25).

Workup

  1. customproduced

Sources & evidence

ORD record
ord-c8f075a893be41daaa56c130dedf18be
Source dataset
uspto-grants-2013_06
Patent number
US08471004B2

Reaction notes

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