Acetic Anhydride → HCID 16736941, compound

HRID 913203Notes

Reaction equation

HRID 913203 reaction equation
[C:1](OC(=O)C)(=[O:3])C.[NH2:8][CH2:9][C:10]([N:12]1[CH2:16][C@H:15]([NH:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:14][C@H:13]1[C:26]([OH:28])=[O:27])=[O:11]>C(O)=O>[C:18]([NH:17][C@H:15]1[CH2:16][N:12]([C:10](=[O:11])[CH2:9][NH:8][CH:1]=[O:3])[C@H:13]([C:26]([OH:28])=[O:27])[CH2:14]1)(=[O:25])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 7918Acetic Anhydride2×HCID 16656685Danegaptide2×

Product 1

HCID 16736941HCID 16736941, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Acetic anhydride (Acros) (0.32 mL, 3.4 mmol, 10 equivalents) was added dropwise to a solution of (2S4R)1-(2-Amino-acetyl)-4-benzoylamino-pyrrolidine-2-carboxylic acid (Compound 2, 0.1 g, 0.34 mmol, 1 equivalent) in formic acid (J. T. Baker) (1 mL) at 0° C. After the addition was complete, the reaction mixture was allowed to warm to room temperature and stirred an additional 24 hours. The reaction mixture was monitored by TLC and LCMS. An additional amount of acetic anhydride (0.32 mL, 3.4 mmol, 10 equivalents) was added and the reaction mixture stirred for 24 hours at room temperature. Ice-water (1 mL) was added and the volatiles were removed in vacuo to yield an oily crude product that was further purified by HPLC (column: Waters Atlantis 19×150 mm) using 0.1% formic acid in H2O/MeOH 20-40% MeOH over 15 minute gradient to afford 0.031 g (29%) of the desired product.

Workup

  1. additionAfter the addition
  2. stirringthe reaction mixture stirred for 24 hours at room temperature
  3. customthe volatiles were removed in vacuo
  4. customto yield an oily crude product that
  5. customwas further purified by HPLC (column: Waters Atlantis 19×150 mm)
  6. customover 15 minute

Sources & evidence

ORD record
ord-b415b82a25df4c498f2801122c91782c
Source dataset
uspto-grants-2011_09
Patent number
US08026272B2

Reaction notes

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