Hydrochloric Acid → HCID 54459747, compound

HRID 1451382Notes

Reaction equation

HRID 1451382 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:15]=[CH:14][C:7]([CH2:8][O:9][C:10](=[O:13])[CH2:11][NH2:12])=[CH:6][CH:5]=1.[N:16]1[CH:21]=CC=CC=1.[CH:22]1[C:27]([N+:28]([O-:30])=[O:29])=[CH:26][CH:25]=[C:24]([Cl-]C([O-])=O)[CH:23]=1.CC[O:37]CC>>[CH3:2][O:3][C:4]1[CH:15]=[CH:14][C:7]([CH2:8][O:9][C:10](=[O:13])[CH2:11][NH:12][C:21](=[O:37])[NH:16][C:24]2[CH:23]=[CH:22][C:27]([N+:28]([O-:30])=[O:29])=[CH:26][CH:25]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 3283Diethyl EtherHCID 18956023HCID 18956023, compound

Product 1

HCID 54459747HCID 54459747, compound

Conditions

Temperature
0 °C

Procedure

The HCl salt of glycine 4-methoxybenzyl ester (1 g, 4.3 mmol) to was cooled to 0° C. and 7 mL of pyridine was added. After 10 minutes at 0° C., 4-nitrophenylchloroformate (980 mg, ~1.15 equivalents) was added over 5 minutes. The reaction mixture was stirred at 0° C. for 5 minutes and then allowed to warm to room temperature. After 1.5 hours at room temperature, the reaction mixture was diluted with ether and washed with cold 0.5N HCl and brine. The organic layer was dried over MgSO4 and concentrated under reduced pressure to give 1.5 g of crude product.

Workup

  1. temperatureto warm to room temperature
  2. waitAfter 1.5 hours at room temperature
  3. washwashed with cold 0.5N HCl and brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-11122db324114e11a05c9cc18fde1a9a
Source dataset
uspto-grants-1997_02
Patent number
US05604234

Reaction notes

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