Methylamine → HCID 57078999, compound

HRID 378843Notes

Reaction equation

HRID 378843 reaction equation
[CH:1]([N:4](CC)C(C)C)(C)C.[NH2:10][C:11](=[O:26])[C@@H:12]([NH:18]C(OC(C)(C)C)=O)[CH2:13][CH2:14][C:15]([OH:17])=O.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.CN>C(#N)C>[NH2:18][C@@H:12]([CH2:13][CH2:14][C:15]([NH:4][CH3:1])=[O:17])[C:11]([NH2:10])=[O:26]

Participants

6

Reactant 4

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 2734757HCID 2734757, compound

Product 1

HCID 57078999HCID 57078999, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N,N-Diisopropylethylamine (2.0 ml) was added to a solution of (4S)-5-amino-4-[[(1,1-dimethylethoxy)carbonyl]amino]-5-oxo-pentanoic acid (0.49 g), bromo-tris-pyrrolidino-phosphonium hexafluorophosphate (1.20 g) and methylamine (0.16 g) in acetonitrile (20 ml). The reaction mixture was stirred at room temperature for 2 hours then concentrated. The residue was taken into 4M HCl in 1,4-dioxane (20 ml), stirred for 4 hours then concentrated. Purification (Preparative C18 125 Å bulk packing material, water:methanol, gradient elution 0:100 to 100:0) gave the sub-title compound (0.48 g).

Workup

  1. concentrationthen concentrated
  2. stirringstirred for 4 hours
  3. concentrationthen concentrated
  4. customPurification (Preparative C18 125 Å bulk packing material, water:methanol, gradient elution 0:100 to 100:0)

Sources & evidence

ORD record
ord-2f96ec74444b43a9a6cf74a9f89372b2
Source dataset
uspto-grants-2001_10
Patent number
US06297232B1

Reaction notes

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