Trifluoroacetic acid → HCID 131719931, compound

HRID 977020Notes

Reaction equation

HRID 977020 reaction equation
C(OC([NH:8][CH2:9][C:10]1[CH:45]=[CH:44][C:13]([C:14]([NH:16][NH:17][C:18]([C:20]2[CH:34]=[CH:33][C:23]([O:24][CH2:25][C:26]([O:28]C(C)(C)C)=[O:27])=[C:22]([O:35][CH2:36][C:37]([O:39]C(C)(C)C)=[O:38])[CH:21]=2)=[O:19])=[O:15])=[CH:12][CH:11]=1)=O)(C)(C)C.[C:46]([OH:52])([C:48]([F:51])([F:50])[F:49])=[O:47]>O>[F:49][C:48]([F:51])([F:50])[C:46]([OH:52])=[O:47].[NH2:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]([NH:16][NH:17][C:18]([C:20]2[CH:34]=[CH:33][C:23]([O:24][CH2:25][C:26]([OH:28])=[O:27])=[C:22]([O:35][CH2:36][C:37]([OH:39])=[O:38])[CH:21]=2)=[O:19])=[O:15])=[CH:44][CH:45]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 19610541HCID 19610541, compound

Product 1

HCID 131719931HCID 131719931, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of t-butyl 4-[3-(4-t-butoxycarbonylaminomethylbenzoyl)carbazoyl]-2-(t-butoxycarbonylmethoxy)phenoxyacetate (100 mg) in a mixture of TFA (9 ml) and water (1 ml) was stored at ambient temperature for 2 hours. The reaction mixture was evaporated to near dryness and excess dry ether was added. The solvents were again removed in vacuo. The solid product was triturated with dry ether, collected and dissolved in 50% aqueous acetic acid (10 ml) with gentle warming. The solution was diluted with water (10 ml) and washed with ether (2×20 ml). The aqueous solution was filtered, diluted with water (20 ml) and lyophilised overnight to give the title compound (69 mg) as a white fluffy solid; NMR Spectrum (DHSO-d6) 4.08 (2H, s), 4.60 (2H, s), 4.62 (2H, s), 6.95 (1H, m), 7.4-7.6 (4H, m), 7.92 (2H, m); Mass Spectrum m/Z 418 (H +H)+ ;

Workup

  1. customThe reaction mixture was evaporated
  2. additionwas added
  3. customThe solvents were again removed in vacuo
  4. customThe solid product was triturated with dry ether
  5. customcollected
  6. dissolutiondissolved in 50% aqueous acetic acid (10 ml) with gentle warming
  7. additionThe solution was diluted with water (10 ml)
  8. washwashed with ether (2×20 ml)
  9. filtrationThe aqueous solution was filtered
  10. additiondiluted with water (20 ml)
  11. waitlyophilised overnight

Sources & evidence

ORD record
ord-4ee4d15a301d46bea291aa6af44ed19b
Source dataset
uspto-grants-1997_03
Patent number
US05612373

Reaction notes

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