Hydrazine hydrate (1:1) → HCID 53393733, compound

HRID 60883Notes

Reaction equation

HRID 60883 reaction equation
C[O:2][C:3](=O)[C@@H:4]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[NH2:5].O.[NH2:16][NH2:17]>CO>[NH2:5][C@@H:4]([C:3]([NH:16][NH2:17])=[O:2])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 735796Methyl D-tyrosinate

Product 1

HCID 53393733HCID 53393733, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

D-Tyrosine methyl ester (30 g, 129 mmol, 99% ee) was dissolved in 150 mL of methanol and stirred until dissolved. Hydrazine hydrate (23 ml, 453 mmol) was then added and solution stirred overnight. Methanol was removed at reduced pressure and saturated NaHCO3 was added (150 ml). The product was precipitated, filtered and dried to yield the title compound as a white powder (23.5 g, 93%). 1H NMR (CD3OD, 400 MHz) δ 7.03 (ad, J=8.8 Hz, 2H), 6.72 (ad, J=8.8 Hz, 2H), 3.44 (t, J=6.8 Hz, 1H), 2.91-2.86 (m, 1H), 2.76-2.71 (m, 1H). ESI-MS (m/z): 196.1 [M+1]+.

Workup

  1. dissolutionuntil dissolved
  2. stirringsolution stirred overnight
  3. customMethanol was removed at reduced pressure and saturated NaHCO3
  4. additionwas added (150 ml)
  5. customThe product was precipitated
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-793b114018ea4faba794c52ede8c2a76
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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