Diisopropylethylamine → HCID 66713463, compound

HRID 2063449Notes

Reaction equation

HRID 2063449 reaction equation
[NH:1]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@H:2]([C:6]([OH:8])=O)[CH:3]([CH3:5])[CH3:4].CC[N:18]([CH:22]([CH3:24])C)[CH:19]([CH3:21])C.[CH:25]1[CH:30]=C2N=NN(O)C2=[CH:27][CH:26]=1.O.CC[N:38]=C=NCCCN(C)C.Cl.[C:48]([O-:51])(O)=[O:49].[Na+]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:30]([O:51][C:48]([N:18]1[CH2:19][CH2:21][N:38]([C:6](=[O:8])[C@@H:2]([NH:1][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:3]([CH3:4])[CH3:5])[CH2:24][CH2:22]1)=[O:49])[CH2:25][CH2:26][CH3:27]

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 83693Boc-L-ValineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 66713463HCID 66713463, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of Boc-(L)-Val-OH (400 mg) in DCM (12 mL) were added DIPEA (0.991 mL), DMAP (22 mg), HOBT hydrate (298 mg), EDCI hydrochloride (423 mg) and intermediate 1.4 (343 mg). The mixture was stirred at RT for 6 h. An aq. NaHCO3 solution was added to the mixture and the phases were separated. The org. phase was washed with brine, dried (MgSO4) and evaporated off to afford 844 mg of the desired compound as beige oil.

Workup

  1. customthe phases were separated
  2. washphase was washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated off

Sources & evidence

ORD record
ord-7ca84f1e308244dd89092b0612b7c787
Source dataset
uspto-grants-2012_10
Patent number
US08288385B2

Reaction notes

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