Triethylamine → HCID 67768232, compound

HRID 2396087Notes

Reaction equation

HRID 2396087 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:19][S:20][C:21]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:10][N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([OH:15])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C)CCCN=C=NCC.O.[OH:52]N1C2C=CC=CC=2N=N1.[Cl:62][C:63]1[C:70]([Cl:71])=[CH:69][CH:68]=[CH:67][C:64]=1[CH2:65][NH2:66].CCN(CC)CC>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:19][S:20][C:21]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[CH2:10][N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([OH:15])=[O:14])=[O:7])([CH3:4])([CH3:2])[CH3:3].[Cl:62][C:63]1[C:70]([Cl:71])=[CH:69][CH:68]=[CH:67][C:64]=1[C:65]([NH2:66])=[O:52]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 5876252,3-DichlorobenzylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 22858731HCID 22858731, compound

Product 1

HCID 67768232HCID 67768232, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

[2(R)-(t-butoxycarbonyl)amino-3-triphenylmethylmercaptopropyl]-L-proline (0.08 g, 0.153 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDC) (0.035 g, 0.184 mmol), and 1-hydroxybenzotriazole hydrate (HOBT) (0.025 g,0.184 mmol) were dissolved in DMF (2 mL), treated with 2,3-dichlorobenzylamine (0.025 mL, 0.184 mmol), and brought to pH 7 with Et3N (0.026 mL, 0.184 mmol). After stirring at ambient temperature for 18 h the mixture was concentrated to dryness, and the residue was partitioned between EtOAc and H2O, the organic layer separated, washed with aq satd NaHCO3, brine, and dried (Na2SO4). Filtration and concentration provided the title compound. 1H NMR (CD3OD) δ 7.1-7.5 (m, 18H), 4.53 (d, 1H, J=8 Hz), 4.26 (d, 1H,J=8 Hz), 3.64-3.76 (m, 1H), 2.96-3.14 (m, 2H), 2.52-2.66 (m, 1H), 2.1-2.5 (m, 5H), 1.6-1.9 (m, 3H), 1.45 (s, 9H).

Workup

  1. concentrationwas concentrated to dryness
  2. customthe residue was partitioned between EtOAc and H2O
  3. customthe organic layer separated
  4. washwashed with aq satd NaHCO3, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-297c3c37e6104a51bbae0f0deb691426
Source dataset
uspto-grants-1996_02
Patent number
US05491164

Reaction notes

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