Trifluoroacetic acid → HCID 131726212, compound

HRID 1375205Notes

Reaction equation

HRID 1375205 reaction equation
[NH:1](C(OC(C)(C)C)=O)[CH2:2][C:3]([NH:5][CH2:6][C:7]([OH:9])=[O:8])=[O:4].[C:17]([OH:23])([C:19]([F:22])([F:21])[F:20])=[O:18]>C(Cl)Cl>[C:17]([OH:23])([C:19]([F:22])([F:21])[F:20])=[O:18].[NH2:1][CH2:2][C:3]([NH:5][CH2:6][C:7]([OH:9])=[O:8])=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 3334662-(2-{[(Tert-butoxy)carbonyl]amino}acetamido)acetic acid

Product 1

HCID 131726212HCID 131726212, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 100 mL media bottle equipped with a septum cap and stir bar was charged with of t-BOC-GlyGly-Ama-diEt (5.12 g, 13.14 mmol) and CH2Cl2(15 mL). With vigorous stirring, TFA (25 mL in 25 mL CH2Cl2) was added dropwise. After 1 hour the reaction was complete, the TFA was removed in vacuo and the trifluoroacetate salt precipitated with Et2O. The TFA-GlyGly-Ama-diEt salt was collected by filteration, washed with Et2O and recrystallized from absolute EtOH:ether (7:3 v/v). The white crystals were dried in vacuo to give 5.21 g of product: 1H NMR (DMSO-d6) δ 8.96 (br d, 1, —NHCH—), 8.63 (br t, 1, —NHCH2—), 8.02 (v br s, 3, NH3CH2), 5.09 (d, 1, CH(CO2Et), 4.12−4.24 (m, 4, OCH2CH3), 3.94 (br d, 2, —NHCH2—), 3.59 (br s, 2, —NHCH2—), 1.21 (t, 6, OCH2CH3). 13C NMR (CDCl3) δ 168.8, 166.4, 158.3, 158.0, 119.3, 115.4, 61.9, 56.3, 41.5, 13.9.

Workup

  1. customA 100 mL media bottle equipped with a septum
  2. customcap
  3. customthe TFA was removed in vacuo
  4. customthe trifluoroacetate salt precipitated with Et2O
  5. customThe TFA-GlyGly-Ama-diEt salt was collected by filteration
  6. washwashed with Et2O
  7. customrecrystallized from absolute EtOH:ether (7:3 v/v)
  8. customThe white crystals were dried in vacuo

Sources & evidence

ORD record
ord-1bc5135485cd4e0f820e5af531ee6094
Source dataset
uspto-grants-2007_01
Patent number
US07166733B2

Reaction notes

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