Dimethylformamide → HCID 22884176, compound

HRID 1598473Notes

Reaction equation

HRID 1598473 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][CH2:15][CH3:16])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN=C=NCCC[N:25]([CH3:27])C.Cl.C1C=CC2N(O)N=NC=2C=1.CN([CH:42]=[O:43])C>C(N(CC)CC)C>[CH3:42][O:43][N:25]([CH3:27])[C:10](=[O:12])[C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2733747N-tert-Butoxycarbonyl-L-norleucine

Product 1

HCID 22884176HCID 22884176, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

The title compound was prepared according to the procedure described in Example 1, Step A except using 2(S)-t-butoxycarbonylaminohexanoic acid (10.6 g, 0.045 mol), N, O-dimethylhydroxylamine hydrochloride (4.69 g, 0.048 mol), EDC.HCl (9.45 g, 0.049 mol), HOBT (6.18 g, 0.045 mol), DMF (200 mL) and triethylamine at pH 7. The crude product was chromatographed on silica gel with 15-20% ethyl acetate in hexane. The title compound was obtained as an oil. NMR (DMSO-d6, 300 MHz) δ 7.01 (1H, d, J=8 Hz), 4.34 (1H, q, J=5 Hz), 7.72 (3H, s), 3.09 (3H, s), 1.50 (2H, m), 1.36 (9H, s), 1.17 (3H, m), 0.85 (3H, t, J=6 Hz).

Workup

  1. customThe title compound was prepared
  2. customThe crude product was chromatographed on silica gel with 15-20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-0cbf45663f8d4f18b4292faee9b9da98
Source dataset
uspto-grants-1998_04
Patent number
US05736539

Reaction notes

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