Triethylamine → HCID 178491116, compound

HRID 1898977Notes

Reaction equation

HRID 1898977 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][N:10]([C:15](=[O:34])[C@H:16]([CH2:28][C:29]2[N:33]=[CH:32][NH:31][CH:30]=2)[NH:17][C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:11][C:12]([OH:14])=[O:13])=[CH:5][CH:4]=1.C1C=C2N=NN(O)C2=CC=1.O.C1CCC(N=C=NC2CCCCC2)CC1.Cl.[CH2:62](OC(=O)CN)[C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1.CCN(CC)CC>CN(C=O)C>[C:63]1([CH2:62][O:13][C:12](=[O:14])[CH2:11][N:10]([CH2:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:15](=[O:34])[C@H:16]([CH2:28][C:29]2[N:33]=[CH:32][NH:31][CH:30]=2)[NH:17][C:18]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:19])[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 11701227Benzyl 2-aminoacetate hydrochlorideHCID 178491120HCID 178491120, compound

Product 1

HCID 178491116HCID 178491116, compoundYield 59.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the acid from Step 3 (0.41 g, 0.88 mmol) in DMF (5 mL) was added HOBT hydrate (0.16 g, 1.05 mmol) and DCC (0.22 g, 1.05 mmol) followed by glycine benzyl ester hydrochloride (0.18 g, 0.88 mmol). Et3N (0.12 mL, 0.88 mmol) was added and the mixture was stirred overnight at room temperature. The mixture was filtered, the filtrate was diluted with CHCl3, washed twice with saturated NaHCO3, brine, dried over MgSO4, and concentrated. Flash chromatography (2-5% MeOH/CHCl3) gave 0.29 g (54%) of the title compound as a white foam; ES-MS 614 (m+1).

Workup

  1. filtrationThe mixture was filtered
  2. additionthe filtrate was diluted with CHCl3
  3. washwashed twice with saturated NaHCO3, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2cece60c23a046c6b6ca2316d3137243
Source dataset
uspto-grants-1996_11
Patent number
US05571792

Reaction notes

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