Hydrazine hydrate (1:1) → HCID 57808442, compound

HRID 2105174Notes

Reaction equation

HRID 2105174 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[N:7][C:8]([C:15]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:16])=[CH:9][C:10]=1[CH2:11][CH:12]([CH3:14])[CH3:13])=O.O.[NH2:24][NH2:25]>C(O)C>[CH2:11]([C:10]1[CH:9]=[C:8]([C:15]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:16])[N:7]=[N:6][C:5]=1[C:3]([NH:24][NH2:25])=[O:2])[CH:12]([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 11645176HCID 11645176, compound

Product 1

HCID 57808442HCID 57808442, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mono-methyl ester 5 (10 mg, 0.033 mmol) was dissolved in 3.5 mL anhydrous ethanol (dried over 4 Å molecular sieves). Hydrazine hydrate was added (55 μL, 1.65 mmol, 53 mg), and the reaction was stirred for 5.5 hours at room temperature under an atmosphere of nitrogen. The volatiles were evaporated under reduced pressure, and the product oil was triturated three times with ca. 3 mL diethyl ether. The bright yellow oil was dried under high vacuum to produce a 10 mg (quant.) of a pale yellow solid. MS: (ESI-TOF) MH+ expected: 306.1924, found: 306.1923.

Workup

  1. customThe volatiles were evaporated under reduced pressure
  2. customthe product oil was triturated three times with ca. 3 mL diethyl ether
  3. customThe bright yellow oil was dried under high vacuum
  4. customto produce a 10 mg (quant.) of a pale yellow solid

Sources & evidence

ORD record
ord-aeece25ec5134fac98726b6e5d05130c
Source dataset
uspto-grants-2009_08
Patent number
US07579350B2

Reaction notes

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