Hydrochloric Acid → 3-[2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)acetamido]benzoic acid

HRID 1434486Notes

Reaction equation

HRID 1434486 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].C(N(C(C)C)C(C)C)C.[C:20]([NH:37][CH2:38][C:39](Cl)=[O:40])([O:22][CH2:23][CH:24]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:30]2[C:25]1=[CH:26][CH:27]=[CH:28][CH:29]=2)=[O:21].Cl>C1COCC1.C(Cl)Cl>[CH:26]1[C:25]2[CH:24]([CH2:23][O:22][C:20]([NH:37][CH2:38][C:39]([NH:1][C:2]3[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=3)[C:5]([OH:7])=[O:6])=[O:40])=[O:21])[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:30]=2[CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 74193-Aminobenzoic AcidHCID 81531DiisopropylethylamineHCID 11758879Fmoc-Gly-Cl

Product 1

HCID 669667263-[2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)acetamido]benzoic acidYield 43%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-aminobenzoic acid (0.5 g; 3.8 mmol) and N-ethyldiisopropylamine (DIEA) (0.64 mL; 3.8 mmol) in THF (20 mL) was added dropwise to a solution of Fmoc-glycine chloride (1.2 g; 4.0 mmol) (3) in THF (10 mL) and CH2Cl2 (10 mL). After 24 h stirring at room temperature 1 M HCl (50 mL) was added (final pH: 1.5). The precipitate was filtered, washed with H2O (2×100 mL), vacuum dried and crystallised from CHCl3/CH3OH (1:1) to give B as a white solid (0.7 g; 1.6 mmol). Yield 43%.

Workup

  1. additionwas added (final pH: 1.5)
  2. filtrationThe precipitate was filtered
  3. washwashed with H2O (2×100 mL), vacuum
  4. customdried
  5. customcrystallised from CHCl3/CH3OH (1:1)
  6. customto give B as a white solid (0.7 g; 1.6 mmol)

Sources & evidence

ORD record
ord-b361f265b5dd41ddb6320f9ca05cbd5e
Source dataset
uspto-grants-2009_11
Patent number
US07611692B2

Reaction notes

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