Methyl chloroformate → HCID 91325138, compound

HRID 411545Notes

Reaction equation

HRID 411545 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[NH2:6][C@H:7]([CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]#[N:35])=[CH:30][CH:29]=1)[CH2:8][N:9]1[CH2:15][CH:14]2[CH:16]([N:17]([CH3:25])[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH:11]([CH2:12][CH2:13]2)[CH2:10]1.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[C:20]([O:19][C:18]([N:17]([CH3:25])[CH:16]1[CH:11]2[CH2:12][CH2:13][CH:14]1[CH2:15][N:9]([CH2:8][C@H:7]([NH:6][C:2](=[O:3])[O:4][CH3:5])[CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]#[N:35])=[CH:30][CH:29]=1)[CH2:10]2)=[O:24])([CH3:22])([CH3:21])[CH3:23]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 10340Sodium CarbonateHCID 20583396HCID 20583396, compound

Product 1

HCID 91325138HCID 91325138, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl chloroformate (0.24 mL, 3.2 mmol) was added, at 0° C., to a mixture of tert-butyl 3-[(2S)-2-amino-3-(4-cyanophenoxy)propyl]-3-azabicyclo[3.2.1]oct-8-yl(methyl)carbamate (see step (vii) above; 1.2 g, 2.9 mmol) and TEA (1.2 mL, 9 mmol) in DCM (30 mL). The mixture was allowed to reach rt over the course of 3 h, after which time a saturated solution of Na2CO3 was added. The organic phase was separated, dried and evaporated to give a crude product that was purified by chromatography on silica gel. This gave 0.6 g (45%) of the sub-title compound.

Workup

  1. customto reach rt over the course of 3 h
  2. customThe organic phase was separated
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-1c0ffbde59f142a1bfb4e3ac42c22862
Source dataset
uspto-grants-2003_05
Patent number
US06559162B2

Reaction notes

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