Methanol → HCID 178451783, compound

HRID 1245618Notes

Reaction equation

HRID 1245618 reaction equation
[NH2:1][NH2:2].C([O:5][C:6](=O)[CH:7]([C:21](=O)[C:22]([F:25])([F:24])[F:23])[CH:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1)C.CO>C1(C)C=CC=CC=1>[C:17]([O:16][C:14]([N:11]1[CH2:12][CH2:13][CH:8]([C:7]2[C:6]([OH:5])=[N:1][NH:2][C:21]=2[C:22]([F:25])([F:24])[F:23])[CH2:9][CH2:10]1)=[O:15])([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 887MethanolHCID 9321HydrazineHCID 69666019HCID 69666019, compound

Product 1

HCID 178451783HCID 178451783, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

Anhydrous hydrazine (0.040 mL, 41 mg, 1.27 mmol) was added to a stirred solution of 1-(tert-butoxycarbonyl)-α-(trifluoroacetyl)-4-piperidineacetic acid ethyl ester (275 mg, 0.75 mmol, from Step B) in toluene (2.0 mL) at RT. The mixture was warmed to 60° C. for 4 h, followed by 16 h at 80° C. The mixture was allowed to cool to RT, transferred to another flask with CH3OH, and evaporated to give the title compound as a white solid. For the title compound: 1H NMR (500 MHz, CD3OD) δ 4.15 (bd, J=13, 2H), 2.86–2.70 (m, 3H), 1.88 (bq, J=12, 2H), 1.62 (bd, J=13, 2H), 1.47 (s, 9H); ESI-MS 280.3 (M+H−56) and 236.3 (M+H−100); HPLC A: 3.0 min.

Workup

  1. temperatureto cool to RT
  2. customevaporated

Sources & evidence

ORD record
ord-18912dae09e24c2b9ddb1a2e12c7c84d
Source dataset
uspto-grants-2006_10
Patent number
US07125887B2

Reaction notes

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