Glycolic Acid → HCID 67491180, compound

HRID 245108Notes

Reaction equation

HRID 245108 reaction equation
CCN=C=NCCCN(C)C.Cl.[CH2:13]([C:15]1[CH:27]=[C:26]([C:28]2[N:32]=[C:31]([C:33]3[CH:38]=[C:37]([O:39][CH3:40])[N:36]=[C:35]([CH:41]([CH2:44][CH3:45])[CH2:42][CH3:43])[CH:34]=3)[O:30][N:29]=2)[CH:25]=[C:24]([CH3:46])[C:16]=1[O:17][CH2:18][C@@H:19]([OH:23])[CH2:20][NH:21][CH3:22])[CH3:14].[C:47]([OH:51])(=O)[CH2:48][OH:49].C1C=CC2N(O)N=NC=2C=1>C1COCC1>[CH2:13]([C:15]1[CH:27]=[C:26]([C:28]2[N:32]=[C:31]([C:33]3[CH:38]=[C:37]([O:39][CH3:40])[N:36]=[C:35]([CH:41]([CH2:44][CH3:45])[CH2:42][CH3:43])[CH:34]=3)[O:30][N:29]=2)[CH:25]=[C:24]([CH3:46])[C:16]=1[O:17][CH2:18][C@@H:19]([OH:23])[CH2:20][N:21]([CH3:22])[C:47](=[O:51])[CH2:48][OH:49])[CH3:14]

Participants

6

Reactant 4

HCID 757Glycolic AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67491127HCID 67491127, compound

Product 1

HCID 67491180HCID 67491180, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

EDC hydrochloride (144 mg, 753 μmol) is added to a stirred solution of (2S)-1-(2-ethyl-4-{5-[2-(1-ethyl-propyl)-6-methoxy-pyridin-4-yl]-[1,2,4]oxadiazol-3-yl}-6-methyl-phenoxy)-3-methylamino-propan-2-ol (294 mg, 627 μmol), glycolic acid (57 mg, 753 μmol) and HOBt (101 mg, 753 μmol) in THF (10 mL). The mixture is stirred at rt for 2 h before it is concentrated. The crude product is purified by prep. HPLC, then on prep. TLC plates using DCM containing 10% of 7 N NH3 in methanol to give the title compound (149 mg) as a white solid; LC-MS: tR=1.14 min, [M+H]+=527.17; 1H NMR (CDCl3): δ0.84 (t, J=7.5 Hz, 6H), 1.33 (t, J=7.5 Hz, 3H), 1.69-1.88 (m, 4H), 2.40 (s, 3H), 2.57-2.66 (m, 1H), 2.76 (q, J=7.5 Hz, 2H), 3.10 (s, 3H), 3.76 (d, J=5.3 Hz, 2H), 3.80-3.88 (m, 1H), 3.89-3.94 (m, 1H), 4.02 (s, 3H), 4.25 (s, 2H), 4.28-4.36 (m, 1H), 7.33 (s, 1H), 7.45 (s, 1H), 7.88 (s, 1H), 7.89 (s, 1H).

Workup

  1. concentrationis concentrated
  2. customThe crude product is purified by prep

Sources & evidence

ORD record
ord-f4f49585f84f412e9edc735dc006b6e2
Source dataset
uspto-grants-2014_02
Patent number
US08658675B2

Reaction notes

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