Dimethylformamide → HCID 86735590, compound

HRID 1679786Notes

Reaction equation

HRID 1679786 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][C@H:6]([C:8]([NH:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[O:9])[CH3:7])=[O:4].FC(F)(F)[C:18]([OH:20])=[O:19].COC(=O)CN[C:28](=O)[C@H:29]([CH3:35])NC(=O)CN.C([N:40]1[CH2:45][CH2:44][O:43]CC1)C.[CH3:46]N(C)C=O>>[CH3:15][O:14][C:12](=[O:13])[CH2:11][NH:10][C:8](=[O:9])[C@H:6]([CH3:7])[NH:5][C:3](=[O:4])[CH2:2][NH:1][C:44](=[O:43])[CH2:45][NH:40][C:18]([O:20][C:29]([CH3:35])([CH3:46])[CH3:28])=[O:19]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 7525EthylmorpholineHCID 54222962HCID 54222962, compoundHCID 86735587HCID 86735587, compound

Product 1

HCID 86735590HCID 86735590, compound

Procedure

To a cold (ice bath), stirred solution of H-Gly-Ala-Gly-OMe.CH3CO2H (6.4 g, 20.03 mmoles, described in Example 3) in dimethylformamide (30 ml) is added N-ethylmorpholine (2.8 ml) followed by a solution of Boc-Gly-OTcp (8.5 g; 24 mmoles) in dimethylformamide (20 ml). The solution is kept in an ice bath for 2 days. The solvent is evaporated, the residue dissolved in methanol and the product precipitated with diethyl ether. Crystallization from ethyl acetate gives the title compound; mp 103° - 105° and 141° C (dimorphic); nmr 1.25 δ (3H), 1.38 δ (9H), 3.65 δ (3H).

Workup

  1. customThe solvent is evaporated
  2. dissolutionthe residue dissolved in methanol
  3. customthe product precipitated with diethyl ether
  4. customCrystallization from ethyl acetate

Sources & evidence

ORD record
ord-082f338e6dd041d6a5ebc818546993b0
Source dataset
uspto-grants-1978_03
Patent number
US04081530

Reaction notes

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