Hydrochloric Acid → HCID 22951555, compound

HRID 276736Notes

Reaction equation

HRID 276736 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([O:18][CH3:19])=[O:17])[CH:11]=1)[C:4]([NH2:6])=[O:5].[CH3:20][C:21]1[CH:22]=[C:23]([CH:45]=[CH:46][CH:47]=1)[CH2:24][C@@H:25]([C:42](O)=[O:43])[NH:26][C:27](=[O:41])[CH:28]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.O.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.CN(C)CCCN=C=NCC.Cl>C(Cl)Cl>[CH3:19][O:18][C:16]([C:12]1[CH:11]=[C:10]([CH2:9][CH2:8][CH2:7][C@H:3]([NH:2][C:42](=[O:43])[C@H:25]([CH2:24][C:23]2[CH:45]=[CH:46][CH:47]=[C:21]([CH3:20])[CH:22]=2)[NH:26][C:27](=[O:41])[CH:28]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:4]([NH2:6])=[O:5])[CH:15]=[CH:14][CH:13]=1)=[O:17]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 53706240HCID 53706240, compoundHCID 69266366HCID 69266366, compound

Product 1

HCID 22951555HCID 22951555, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-2-amino-5-(3-carbomethoxyphenyl)-pentanamide HCl (0.30 g, 0.80 mmol), of 3-methyl-N-(2,2-diphenylacetyl)-L-phenylalanine (0.23 g, 0.80 mmol), 1-hydroxybenzotriazole hydrate (0.135 g, 0.89 mmol) and N-methylmorpholine (0.35 ml, 3.2 mmol) in CH2Cl2 (25 mL) is added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide.HCl (0.23 g, 1.2 mmol) in one portion, and the mixture is stirred at room temperature for 16 hours. The solution is then washed with 1 N HCl (100 mL), saturated aqueous NaHCO3 (1×50 mL), water (1×50 mL) and brine (1×50 mL), dried over MgSO4, and evaporated. The residual solid is triturated with ether to yield N-[4-(3-methoxycarbonyl-phenyl)-1(S)-(aminocarbonyl)-butyl]-3-methyl-Nα-(2,2-diphenylacetyl)-L-phenylalaninamide as a light yellow solid.

Workup

  1. washThe solution is then washed with 1 N HCl (100 mL), saturated aqueous NaHCO3 (1×50 mL), water (1×50 mL) and brine (1×50 mL)
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customThe residual solid is triturated with ether

Sources & evidence

ORD record
ord-78417c80acc84ba7a9c277d9dc4fa92e
Source dataset
uspto-grants-2002_03
Patent number
US06353017B1

Reaction notes

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