Triethylamine → HCID 22873002, compound

HRID 2293448Notes

Reaction equation

HRID 2293448 reaction equation
[CH3:1][C:2]([CH3:22])([O:4][C:5]([NH:7][C@@H:8]([CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:9][N:10]1[CH2:17][CH2:16][CH2:15][C@H:11]1[C:12]([OH:14])=O)=[O:6])[CH3:3].C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.[C:55]1([CH2:61][CH2:62][CH2:63][CH2:64][NH2:65])[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1>CN(C1C=CN=CC=1)C.CN(C=O)C.C(Cl)Cl>[C:55]1([CH2:61][CH2:62][CH2:63][CH2:64][NH:65][C:12](=[O:14])[C@@H:11]2[CH2:15][CH2:16][CH2:17][N:10]2[CH2:9][C@@H:8]([NH:7][C:5]([O:4][C:2]([CH3:1])([CH3:3])[CH3:22])=[O:6])[CH2:18][CH:19]([CH3:21])[CH3:20])[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 83242BenzenebutanamineHCID 15235098HCID 15235098, compound

Product 1

HCID 22873002HCID 22873002, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Using the procedure described in ample 1e, a solution of 1-[2-(S)-[[(1,1-dimethylethoxy)carbonyl]amino]-4-methylpentyl]-L-proline (200 mg), DCC (197 mg, 0.955 mmol), DMAP (102 mg, 0.83 mmol), HOBT (155 mg, 1.012 mmol), triethylamine (177 uL, 1.27 mmol) in DMF (1.0 mL) and CH2Cl2 (2 mL) was treated with 4-phenylbutylamine (150 uL) to provide 233 mg (82%) of the title compound. The 1H NMR and Mass spectrum analysis of this compound was consistent with the structure.

Sources & evidence

ORD record
ord-770d2a13284e4728be4f2ce26454cbad
Source dataset
uspto-grants-1997_11
Patent number
US05686469

Reaction notes

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