Dimethylformamide → HCID 86735588, compound

HRID 1679784Notes

Reaction equation

HRID 1679784 reaction equation
[NH2:1][C@H:2]([C:4]([NH:6][CH2:7][C:8]([O:10][CH3:11])=[O:9])=[O:5])[CH3:3].FC(F)(F)[C:14]([OH:16])=[O:15].COC(=O)CN[C:24](=O)[C@H:25]([CH3:27])N.C([N:32]1[CH2:37][CH2:36][O:35]CC1)C.[CH3:38]N(C)C=O>>[CH3:11][O:10][C:8](=[O:9])[CH2:7][NH:6][C:4](=[O:5])[C@H:2]([CH3:3])[NH:1][C:36](=[O:35])[CH2:37][NH:32][C:14]([O:16][C:25]([CH3:27])([CH3:38])[CH3:24])=[O:15]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 7525EthylmorpholineHCID 13875061Methyl L-alanylglycinateHCID 88813774HCID 88813774, compound

Product 1

HCID 86735588HCID 86735588, compound

Procedure

To a cold (ice bath) solution of H-Ala-Gly-OMe.CH3CO2H (45 mmoles, described in Example 1) in dimethylformamide (50 ml) is added N-ethylmorpholine (pH~8) followed by a cold solution of Boc-Gly-OTcp (18 g, 45 mmoles) in dimethylformamide (50 ml). The solution is kept in an ice bath for 2 days. The solvent is evaporated and the product purified by column chromatography on silica gel using ethyl acetate-methanol-pyridine 98:1:1. The product is crystallized from ethyl acetate-petroleum ether to give the title compound; m.p. 98° - 100° C; nmr (DMSO-d6); 1.25 δ (3H), 1.4 δ (9H), 3.68 δ (3H).

Workup

  1. customThe solvent is evaporated
  2. customthe product purified by column chromatography on silica gel
  3. customThe product is crystallized from ethyl acetate-petroleum ether

Sources & evidence

ORD record
ord-1cd7cd54947c435c8b9ce26aa371c7bd
Source dataset
uspto-grants-1978_03
Patent number
US04081530

Reaction notes

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