Boc-L-Valine → HCID 86760634, compound

HRID 1394052Notes

Reaction equation

HRID 1394052 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH:13]([CH3:15])[CH3:14])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.C(N=C=NCCCN(C)C)C.[Cl:28][C:29]1[CH:30]=[C:31]([CH:39]=[CH:40][C:41]=1[Cl:42])[O:32][CH:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:28][C:29]1[CH:30]=[C:31]([CH:39]=[CH:40][C:41]=1[Cl:42])[O:32][CH:33]1[CH2:38][CH2:37][N:36]([C:10]([C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH:13]([CH3:15])[CH3:14])=[O:12])[CH2:35][CH2:34]1

Participants

6

Reactant 4

HCID 83693Boc-L-ValineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 37320424-(3,4-Dichlorophenoxy)piperidine

Product 1

HCID 86760634HCID 86760634, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To (2S)-2-[(tert-butoxycarbonyl)amino]-3-methylbutanoic acid (1.13 g) in CH2Cl2 (5 ml) was added 1-ethyl-3-[3-(dimethylamino)-propyl]carbodiimide hydrochloride (0.99 g) and left to stir for 5 mins. The product of Example 1, Step (b) (0.98 g) dissolved in CH2Cl2 (5 ml) was then and the reaction left to stir for 3 hrs. Aqueous NaHCO3 solution was added and the product extracted with ethyl acetate. The organic phase was dried, filtered and evaporated to give the sub-title compound (1.57 g).

Workup

  1. waitleft
  2. waitthe reaction left
  3. stirringto stir for 3 hrs
  4. extractionthe product extracted with ethyl acetate
  5. customThe organic phase was dried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-a64284a3f9b94884b2b8281544f23aff
Source dataset
uspto-grants-2008_03
Patent number
US07348341B2

Reaction notes

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