Potassium Hydroxide → tert-butyl (S)-1-(carbamoylmethylamino)-3-cyclohexyl-propan-2-ylcarbamate

HRID 1254249Notes

Reaction equation

HRID 1254249 reaction equation
Cl.[NH2:2][CH2:3][C:4]([NH2:6])=[O:5].[OH-].[K+].[CH:9]1([CH2:15][C@H:16]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH:17]=O)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.C([BH3-])#N.[Na+]>CO>[C:4]([CH2:3][NH:2][CH2:17][C@@H:16]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:15][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)(=[O:5])[NH2:6]

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 2723639Glycinamide hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 10848617(S)-Tert-butyl 1-cyclohexyl-3-oxopropan-2-ylcarbamate

Product 1

HCID 57544928tert-butyl (S)-1-(carbamoylmethylamino)-3-cyclohexyl-propan-2-ylcarbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 2-aminoacetamide hydrochloride (0.13 g, 1.13 mmol) in MeOH (1 mL) was added KOH (18 mg). When the solid had completely dissolved, the tert-butyl (S)-2-cyclohexyl-1-formylethylcarbamate from Step 1 was added in one portion, and the resulting suspension was stirred for 15 minutes. A solution of sodium cyanoborohydride (0.18 g, 2.7 mmol) in MeOH (1 mL) was added dropwise. The resulting solution was stirred at rt until no aldehyde remained (˜40 min). The solvent was removed under vacuum and the residue was distributed between ether and water (10 mL/10 mL). The water layer was extracted with ether (2×5 mL). The combined ether layers were dried, and solvent was removed under vacuum to give tert-butyl (S)-1-(carbamoylmethylamino)-3-cyclohexyl-propan-2-ylcarbamate as an oil, which was used for the next step without purification. MS ESI +ve m/z 314 (M+1).

Workup

  1. dissolutionWhen the solid had completely dissolved
  2. custom(˜40 min)
  3. customThe solvent was removed under vacuum
  4. extractionThe water layer was extracted with ether (2×5 mL)
  5. dry with materialThe combined ether layers were dried
  6. customsolvent was removed under vacuum

Sources & evidence

ORD record
ord-e0ef5aa3aa4544cfbbde8bacf0734411
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

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