Water → HCID 21545310, compound

HRID 1605824Notes

Reaction equation

HRID 1605824 reaction equation
[C:1]([NH:20][CH2:21][C:22]([OH:24])=[O:23])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:32][CH2:33]I.O>CN(C)C=O>[Cl:32][CH2:33][O:23][C:22](=[O:24])[CH2:21][NH:20][C:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 11644ChloroiodomethaneHCID 248898N-Tritylglycine

Product 1

HCID 21545310HCID 21545310, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of N-tritylglycine (25.6 g) and triethylamine (14.0 ml) in dimethylformamide (DMF) (60 ml), a solution of chloroiodomethane (24.0 ml) in DMF (40 ml) was added dropwise while stirring, and the mixture was stirred for 3.5 hours at room temperature. Then the mixture was poured into water (400 ml), the organic phase was separated, and the aqueous phase was extracted with ethyl acetate. The combined organic phases were washed with water and thereafter twice with aqueous sodium bicarbonate and again with water. The organic phase was dried and evaporated in vacuo to yield the crude ester. TLC: Rf = 0.7 (cyclohexane-ethyl acetate, 1:1), ir )CHCl3): 1765 cm-1 (ester carbonyl), nmr (CDCl3 -TMS standard): δ = 3.20 (s), 5.53 (s), 7.00-7.30 (m) ppm.

Workup

  1. stirringthe mixture was stirred for 3.5 hours at room temperature
  2. customthe organic phase was separated
  3. extractionthe aqueous phase was extracted with ethyl acetate
  4. washThe combined organic phases were washed with water
  5. customThe organic phase was dried
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-1804a661027742f08b97d39e1f2b4179
Source dataset
uspto-grants-1976_04
Patent number
US03951957

Reaction notes

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