1,2-Dichloroethane → HCID 68508615, compound

HRID 2069459Notes

Reaction equation

HRID 2069459 reaction equation
[C:1]([OH:5])(=O)[CH2:2][OH:3].[CH3:6][CH2:7][N:8](C(C)C)C(C)C.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[CH2:29]([N:31]([CH2:58][CH3:59])[C:32]1[N:37]=[C:36]([C:38]2[O:42][N:41]=[C:40]([C:43]3[CH:48]=[C:47](C)[C:46](OC[C@@H]4CO4)=[C:45](CC)[CH:44]=3)[N:39]=2)[CH:35]=[C:34]([CH3:57])[N:33]=1)[CH3:30]>CN(C=O)C.CCOC(C)=O>[CH2:29]([N:31]([CH2:58][CH3:59])[C:32]1[N:37]=[C:36]([C:38]2[O:42][N:41]=[C:40]([C:43]3[CH:48]=[CH:47][C:46]([CH2:6][CH2:7][NH:8][C:1](=[O:5])[CH2:2][OH:3])=[CH:45][CH:44]=3)[N:39]=2)[CH:35]=[C:34]([CH3:57])[N:33]=1)[CH3:30]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757Glycolic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 86645307HCID 86645307, compound

Product 1

HCID 68508615HCID 68508615, compoundYield 43.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of glycolic acid (33 mg, 0.43 mmol) and DIPEA (146 μL, 0.85 mmol) in DMF (5 mL) is added EDC (82 mg, 0.43 mmol) followed by HOBt (58 mg, 0.43 mmol). The reaction mixture is stirred at rt for 10 min before adding Intermediate 12 (100 mg, 0.28 mmol). Stirring is continued for 18 h and the reaction mixture is then diluted with EtOAc, washed with sat. aq. NaHCO3, dried over MgSO4, filtered and evaporated. The residue is purified by prep. TLC (eluting with DCM/7M NH3 in MeOH 10:1) to give the title compound (50 mg) as a yellow solid; tR=1.05 min; [M+H]+=411.75.

Workup

  1. stirringStirring
  2. waitis continued for 18 h
  3. washwashed with sat. aq. NaHCO3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by prep
  8. washTLC (eluting with DCM/7M NH3 in MeOH 10:1)

Sources & evidence

ORD record
ord-4cd5d0e822264de6a90443977a406433
Source dataset
uspto-grants-2012_10
Patent number
US08299086B2

Reaction notes

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