Glycolic Acid → N-(3-{4-[5-(5-ethyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide

HRID 1094303Notes

Reaction equation

HRID 1094303 reaction equation
[NH2:1][CH2:2][CH:3]([OH:26])[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[S:19][C:20]([CH2:23][CH3:24])=[CH:21][CH:22]=3)[O:15][N:14]=2)=[CH:8][C:7]=1[CH3:25].CCN(C(C)C)C(C)C.[C:36](O)(=[O:39])[CH2:37][OH:38].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(Cl)Cl.CC(=O)OCC>[CH2:23]([C:20]1[S:19][C:18]([C:16]2[O:15][N:14]=[C:13]([C:9]3[CH:10]=[C:11]([CH3:12])[C:6]([O:5][CH2:4][CH:3]([OH:26])[CH2:2][NH:1][C:37](=[O:38])[CH2:36][OH:39])=[C:7]([CH3:25])[CH:8]=3)[N:17]=2)=[CH:22][CH:21]=1)[CH3:24]

Participants

7

Reactant 4

HCID 757Glycolic AcidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 666369791-Amino-3-{4-[5-(5-ethyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenoxy}-propan-2-ol

Product 1

HCID 59202022N-(3-{4-[5-(5-ethyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamideYield 18.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a cold solution (0° C.) of 1-amino-3-{4-[5-(5-ethyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenoxy}-propan-2-ol (32 mg, 86 μmol) in DCM (1 mL), DIPEA (45 mg, 345 μmol), glycolic acid (13 mg, 172 μmol) and finally TBTU (33 mg, 101 μmol) is added. The mixture is stirred at rt for 1 h before it is diluted with EA and washed with water. The aq. phase is extracted back with EA. The combined org. extracts are dried over MgSO4, filtered and evaporated. The crude product is purified by crystallisation from acetonitrile to give N-(3-{4-[5-(5-ethyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide (7 mg) as a white solid; LC-MS: tR=0.95 min, [M+1]+=432.16.

Workup

  1. washwashed with water
  2. extractionThe aq. phase is extracted back with EA
  3. dry with materialextracts are dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product is purified by crystallisation from acetonitrile

Sources & evidence

ORD record
ord-84c70f2cc7054e1a9151fb168450957b
Source dataset
uspto-grants-2012_03
Patent number
US08133910B2

Reaction notes

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