Diisopropylethylamine → (2R,4R)-4-amino-5-biphenyl-4-yl-2-hydroxypentanoic acid ethyl ester

HRID 2045141Notes

Reaction equation

HRID 2045141 reaction equation
CC1OC(=O)O[C:3]=1[CH2:8][O:9][C:10](=[O:29])[C@H:11]([OH:28])[CH2:12][C@H:13]([NH2:27])[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:17][CH:16]=1.OC1C=C(C(O)=O)ON=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:8]([O:9][C:10](=[O:29])[C@H:11]([OH:28])[CH2:12][C@H:13]([NH2:27])[CH2:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[CH:19][CH:20]=1)[CH3:3]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 67969425(2R,4R)-4-amino-5-biphenyl-4-yl-2-hydroxypentanoic acid 5-methyl-2-oxo-[1,3]dioxol-4-ylmethyl esterHCID 178524642HCID 178524642, compound

Product 1

HCID 67969400(2R,4R)-4-amino-5-biphenyl-4-yl-2-hydroxypentanoic acid ethyl esterYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2R,4R)-4-amino-5-biphenyl-4-yl-2-hydroxypentanoic acid 5-methyl-2-oxo-[1,3]dioxol-4-ylmethyl ester (100 mg, 0.3 mmol, 1.0 eq.) and 3-hydroxyisoxazole-5-carboxylic acid (50.5 mg, 391 μmol, 1.5 eq.) were combined in DMF (5 mL) and the resulting mixture was stirred for 2 minutes. DIPEA was added and the resulting mixture was stirred for 1 hour. The material was dried under vacuum then purified using reverse phase chromatography to yield the title compound (40 mg, 98% purity). MS m/z [M+H]+ calc'd for C26H24N2O9, 509.15. found 509.4.

Workup

  1. stirringthe resulting mixture was stirred for 1 hour
  2. customThe material was dried under vacuum
  3. customthen purified

Sources & evidence

ORD record
ord-17347113e5d64c07ba0ac153ddde4839
Source dataset
uspto-grants-2013_11
Patent number
US08586536B2

Reaction notes

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