Glycolic Acid → HCID 59202035, compound

HRID 1094308Notes

Reaction equation

HRID 1094308 reaction equation
[NH2:1][CH2:2][CH:3]([OH:28])[CH2:4][O:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([C:13]2[O:14][C:15]([C:18]3[S:19][C:20]([CH2:23][CH:24]([CH3:26])[CH3:25])=[CH:21][CH:22]=3)=[N:16][N:17]=2)=[CH:8][C:7]=1[CH3:27].CCN(C(C)C)C(C)C.[C:38](O)(=[O:41])[CH2:39][OH:40].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(Cl)Cl.CC(=O)OCC>[OH:41][CH2:38][C:39]([NH:1][CH2:2][CH:3]([OH:28])[CH2:4][O:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([C:13]2[O:14][C:15]([C:18]3[S:19][C:20]([CH2:23][CH:24]([CH3:26])[CH3:25])=[CH:21][CH:22]=3)=[N:16][N:17]=2)=[CH:8][C:7]=1[CH3:27])=[O:40]

Participants

7

Reactant 4

HCID 757Glycolic AcidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66637119HCID 66637119, compound

Product 1

HCID 59202035HCID 59202035, compoundYield 24.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-amino-3-{4-[5-(5-isobutyl-thiophen-2-yl)-[1,3,4]oxadiazol-2-yl]-2,6-dimethyl-phenoxy}-propan-2-ol (109 mg, 271 μmol) in DCM (10 mL), DIPEA (140 mg, 1.086 mmol) and glycolic acid (41 mg, 543 μmol) followed by TBTU (102 mg, 319 μmol) is added at 0° C. The mixture is stirred at rt for 1 h before it is diluted with EA and washed with water. The water phase is separated and extracted once more with EA. The combined org. extracts are dried over MgSO4, filtered and evaporated. The crude product is purified by chromatography on prep. TLC plates with DCM containing 4% of 7 N NH3 in methanol to give 2-hydroxy-N-(2-hydroxy-3-{4-[5-(5-isobutyl-thiophen-2-yl)-[1,3,4]oxadiazol-2-yl]-2,6-dimethyl-phenoxy}-propyl)-acetamide (31 mg) as a white solid; LC-MS: tR=0.94 min, [M+1]+=460.51.

Workup

  1. additionis added at 0° C
  2. washwashed with water
  3. customThe water phase is separated
  4. extractionextracted once more with EA
  5. dry with materialextracts are dried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude product is purified by chromatography on prep

Sources & evidence

ORD record
ord-58b2fb3423ad45648a5cce0b66ecd2b1
Source dataset
uspto-grants-2012_03
Patent number
US08133910B2

Reaction notes

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