Ammonia → HCID 53670432, compound

HRID 581692Notes

Reaction equation

HRID 581692 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([OH:19])=[C:14]([CH:18]=1)[C:15](O)=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].C[N:21]1CCOCC1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[OH-].[NH4+].N>O1CCCC1.C(OCC)(=O)C.C>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([OH:19])=[C:14]([C:15](=[O:16])[NH2:21])[CH:18]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

10

Reactant 6

HCID 222AmmoniaHCID 79724-MethylmorpholineHCID 14923Ammonium HydroxideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 53648305HCID 53648305, compound

Product 1

HCID 53670432HCID 53670432, compound

Reagents, catalysts & solvents 3

HCID 297MethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-(tert-Butoxycarbonylamino-methyl)-2-hydroxy-benzoic acid (20.0 g, 74.9 mmol) in 700 mL tetrahydrofuran at 0° C. was added 4-methyl morpholine (12.3 mL, 112.3 mmol), 1-hydroxybenzo-triazole (15.2 g, 112.3 mmol), followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (21.5 g, 112.3 mmol). Stir for 1 hour at 0° C., then added concentrated ammonium hydroxide (15.2 mL, 112.3 mmol). The reaction was allowed to warm slowly to room temperature and stirred overnight. The reaction was then diluted with ethyl acetate and washed with 5% citric acid (3×250 mL), saturated sodium bicarbonate (3×250 mL), and saturated sodium chloride (1×250 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to yield a pale yellow powder. The powder was collected and washed with ether, followed by drying under reduced pressure to yield (14.0 g, 71%). 1H NMR (400 MHz, DMSO): δ 12.77 (bs, 1H), 8.33 (bs, 1H), 7.72 (d, 1H), 7.28 (d, 2H), 6.84 (d, 1H), 4.05 (d, 2H), 1.38 (s, 9H); Mass Spectrum (Chemical Ionization, 1% NH3 in CH4) m/z 267 (M+H).

Workup

  1. temperatureto warm slowly to room temperature
  2. stirringstirred overnight
  3. washwashed with 5% citric acid (3×250 mL), saturated sodium bicarbonate (3×250 mL), and saturated sodium chloride (1×250 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto yield a pale yellow powder
  8. customThe powder was collected
  9. washwashed with ether
  10. customby drying under reduced pressure
  11. customto yield (14.0 g, 71%)

Sources & evidence

ORD record
ord-d764118ff2a0481b895661a14d22facc
Source dataset
uspto-grants-1999_07
Patent number
US05922697

Reaction notes

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