Glycolic Acid → HCID 44217839, compound

HRID 2037360Notes

Reaction equation

HRID 2037360 reaction equation
[NH2:1][CH2:2][C@H:3]([OH:31])[CH2:4][O:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([C:13]2[N:17]=[C:16]([C:18]3[CH:23]=[C:22]([CH2:24][CH:25]([CH3:27])[CH3:26])[CH:21]=[C:20]([CH3:28])[N:19]=3)[O:15][N:14]=2)=[CH:8][C:7]=1[CH2:29][CH3:30].C1C=CC2N(O)N=NC=2C=1.[C:42](O)(=[O:45])[CH2:43][OH:44].CCN=C=NCCCN(C)C.Cl>C1COCC1.C([O-])(O)=O.[Na+]>[CH2:29]([C:7]1[CH:8]=[C:9]([C:13]2[N:17]=[C:16]([C:18]3[CH:23]=[C:22]([CH2:24][CH:25]([CH3:26])[CH3:27])[CH:21]=[C:20]([CH3:28])[N:19]=3)[O:15][N:14]=2)[CH:10]=[C:11]([CH3:12])[C:6]=1[O:5][CH2:4][C@@H:3]([OH:31])[CH2:2][NH:1][C:43](=[O:44])[CH2:42][OH:45])[CH3:30]

Participants

7

Reactant 4

HCID 757Glycolic AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68628773(S)-1-amino-3-{2-ethyl-4-[5-(4-isobutyl-6-methyl-pyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-propan-2-ol

Product 1

HCID 44217839HCID 44217839, compoundYield 86.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of (S)-1-amino-3-{2-ethyl-4-[5-(4-isobutyl-6-methyl-pyridin-2-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-propan-2-ol (36 mg, 86 μmol), HOBt (14 mg, 103 μmol) and glycolic acid (8 mg, 103 μmol) in THF (3 mL), EDC HCl (20 mg, 103 μmol) is added. The mixture is stirred at rt for 18 h before it is diluted with sat. aq. NaHCO3-solution and extracted twice with EA. The combined org. extracts are dried over MgSO4, filtered and concentrated. The crude product is purified by prep. TLC using DCM containing 11% of methanol to give the title compound (36 mg) as a pale yellow oil; LC-MS: tR=0.98 min, [M+H]+=483.21; 1H NMR (CDCl3): δ 0.98 (d, J=6.3 Hz, 6H), 1.31 (t, J=7.5 Hz, 3H), 1.97-2.08 (m, 1H), 2.38 (s, 3H), 2.59 (d, J=6.8 Hz, 2H), 2.69-2.78 (m, 5H), 2.81 (s br, 1H), 3.42 (s br, 1H). 3.48-3.57 (m, 2H), 3.74-3.93 (m, 2H), 4.17-4.25 (m, 3H), 7.05 (s br, 1H), 7.19 (s, 1H), 7.93 (s, 1H), 7.94 (s, 2H).

Workup

  1. extractionextracted twice with EA
  2. dry with materialextracts are dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product is purified by prep

Sources & evidence

ORD record
ord-2a18635850be44188855017e413f3adc
Source dataset
uspto-grants-2013_11
Patent number
US08575200B2

Reaction notes

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