Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 21070238, compound

HRID 1371541

Reaction equation

HRID 1371541 reaction equation
[C:1]([NH:8][C@H:9]([C:19]([OH:21])=O)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CN([C:25]([O:29][N:30]1N=NC2C=CC=C[C:31]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.Cl.CNOC>C(Cl)Cl>[C:1]([NH:8][CH:9]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]#[N:18])=[CH:15][CH:16]=1)[C:19]([N:30]([O:29][CH3:25])[CH3:31])=[O:21])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

6

Reactant 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 7020841N-(tert-Butoxycarbonyl)-4-cyano-L-phenylalanine

Product 1

HCID 21070238HCID 21070238, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2 g of (N-Boc)-4-cyanophenylalanine, 2.32 g of TBTU, 2.40 ml of DIPEA and 806 mg of N,O-dimethylhydroxylamine hydrochloride are mixed together in 30 ml of DCM. After stirring for 24 hours at RT, the reaction mixture is concentrated to dryness and the residue is then extracted with EtOAc. The organic phase is washed with a pH 2 buffer solution, a saturated NaHCO3 solution and then a saturated NaCl solution. The expected compound crystallizes from a mixture of isopropyl ether and pentane (1.89 g).

Workup

  1. concentrationthe reaction mixture is concentrated to dryness
  2. extractionthe residue is then extracted with EtOAc
  3. washThe organic phase is washed with a pH 2 buffer solution
  4. customThe expected compound crystallizes from a mixture of isopropyl ether and pentane (1.89 g)

Sources & evidence

ORD record
ord-90a6d7c751cc4148b1a4a3cdbb4e6014
Source dataset
uspto-grants-2007_01
Patent number
US07157454B2

Linked notes

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