tert-Butyl isocyanate → HCID 66985254, compound

HRID 1616683Notes

Reaction equation

HRID 1616683 reaction equation
[C:1]([N:5]=[C:6]=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:8][C@@H:9]1[CH2:13][CH2:12][C@@H:11]([C:14]([N:16]2[CH2:23][CH2:22][C@:21]3([CH3:27])[C:24]([CH3:26])([CH3:25])[C@H:17]2[CH2:18][C:19]2[C:31]([OH:32])=[CH:30][CH:29]=[CH:28][C:20]=23)=[O:15])[CH2:10]1.C(N(C(C)C)C(C)C)C>CN(C)C=O>[C:1]([NH:5][C:6]([NH:8][C@@H:9]1[CH2:13][CH2:12][C@@H:11]([C:14]([N:16]2[CH2:23][CH2:22][C@:21]3([CH3:27])[C:24]([CH3:25])([CH3:26])[C@H:17]2[CH2:18][C:19]2[C:31]([OH:32])=[CH:30][CH:29]=[CH:28][C:20]=23)=[O:15])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 62412tert-Butyl isocyanateHCID 81531DiisopropylethylamineHCID 58497679HCID 58497679, compound

Product 1

HCID 66985254HCID 66985254, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

tert-Butylisocyanate (30 mg) is added to a solution of [(1R,3R)-3-amino-cyclopentyl]-[(2R,6S)-10-hydroxy-6,11,11-trimethyl-1,2,5,6-tetrahydro-4H-2,6-methano-benzo[d]azocin-3-yl]-methanone (100 mg) and ethyldiisopropylamine (120 μL) in N,N-dimethylformamide (2 mL). The resulting solution is stirred at 40° C. overnight. Then, the solution is concentrated under reduced pressure and the residue is purified by HPLC on reversed phase (MeCN/H2O/F3CCO2H) to give the title compound.

Workup

  1. concentrationThen, the solution is concentrated under reduced pressure
  2. customthe residue is purified by HPLC on reversed phase (MeCN/H2O/F3CCO2H)

Sources & evidence

ORD record
ord-94c77140f7bb4689a962f5b63ae5a49b
Source dataset
uspto-grants-2014_07
Patent number
US08765780B2

Reaction notes

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