Triethylamine → HCID 70932270, compound

HRID 1873609Notes

Reaction equation

HRID 1873609 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH:10]2[CH2:15][CH2:14][CH2:13][O:12][CH2:11]2)[C:5]([C:16]#[N:17])=[C:4]([S:18][CH2:19][C:20]2[N:21]=[C:22]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)[O:23][CH:24]=2)[N:3]=1.Cl.[CH3:33][O:34][C:35](=[O:39])[CH2:36][NH:37][CH3:38].C(N(CC)CC)C>C1COCC1>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([C:22]2[O:23][CH:24]=[C:20]([CH2:19][S:18][C:4]3[N:3]=[C:2]([N:37]([CH3:38])[CH2:36][C:35]([O:34][CH3:33])=[O:39])[C:7]([C:8]#[N:9])=[C:6]([CH:10]4[CH2:15][CH2:14][CH2:13][O:12][CH2:11]4)[C:5]=3[C:16]#[N:17])[N:21]=2)=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 83544Glycine, N-methyl-, methyl ester, hydrochloride (1:1)HCID 87543039HCID 87543039, compound

Product 1

HCID 70932270HCID 70932270, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

239 mg (0.42 mmol) of the compound from Example 43A are dissolved in 6 ml of dry THF, and 116 mg (0.83 mmol) of sarcosine methyl ester hydrochloride and 126 mg (1.25 mmol) of triethylamine are then added in succession. The reaction mixture is stirred at RT for 10 h. The solvent is then removed on a rotary evaporator and the residue is purified by preparative HPLC (column: YMC GEL ODS-AQ S-5, 15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5).

Workup

  1. customThe solvent is then removed on a rotary evaporator
  2. customthe residue is purified by preparative HPLC (column: YMC GEL ODS-AQ S-5, 15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5)

Sources & evidence

ORD record
ord-7640f6248d49484980f0f227326fcc25
Source dataset
uspto-grants-2012_11
Patent number
US08304412B2

Reaction notes

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