(2S)-2-Aminobutane-1,4-diol → HCID 67092903, compound

HRID 1261846Notes

Reaction equation

HRID 1261846 reaction equation
COC(=O)[C@@H](N(C(OCC1C=CC=CC=1)=O)CC=O)C.N[C@@H](CCO)CO.[CH2:28]([O:35][C:36]([N:38]1[C@@H:47]([CH3:48])[C:46](=[O:49])[N:45]2[CH:40]([O:41][CH2:42][CH2:43][C@H:44]2[CH2:50][OH:51])[CH2:39]1)=[O:37])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>>[CH2:28]([O:35][C:36]([N:38]1[C@@H:47]([CH3:48])[C:46](=[O:49])[N:45]2[C@@H:43]([CH2:44][CH2:50][OH:51])[CH2:42][O:41][CH:40]2[CH2:39]1)=[O:37])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 3

HCID 14325612(2S)-2-Aminobutane-1,4-diolHCID 67093100HCID 67093100, compoundHCID 86638111(S)-2-[Benzyloxycarbonyl-(2-oxo-ethyl)-amino]-propionic acid methyl ester2×

Product 1

HCID 67092903HCID 67092903, compound

Procedure

Condensation of (S)-2-[benzyloxycarbonyl-(2-oxo-ethyl)-amino]-propionic acid methyl ester (intermediate 1) with (S)-2-amino-butane-1,4-diol in analogy with examples 1/2F produced a nearly statistical mixture of the title compound [light yellow gum, MS: 335.5 (M+H)+] and (4S,7S)-4-hydroxymethyl-7-methyl-6-oxo-hexahydro-pyrazino[2,1-b][1,3]oxazine-8-carboxylic acid benzyl ester [light yellow gum, MS: 335.4 (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-defdb1e23e034e86bd93b53854d44f40
Source dataset
uspto-grants-2013_06
Patent number
US08471004B2

Reaction notes

Loading…