Isobutylamine → tert-Butyl ((2S,3R)-3-hydroxy-4-((2-methylpropyl)amino)-1-phenylbutan-2-yl)carbamate

HRID 1505571Notes

Reaction equation

HRID 1505571 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][C@@H:8]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C@H:9]([OH:12])[CH2:10]Cl)([CH3:4])([CH3:3])[CH3:2].[CH2:21]([NH2:25])[CH:22]([CH3:24])[CH3:23].C(=O)([O-])[O-].[Na+].[Na+]>O>[C:1]([O:5][C:6](=[O:20])[NH:7][C@@H:8]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C@H:9]([OH:12])[CH2:10][NH:25][CH2:21][CH:22]([CH3:24])[CH3:23])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6558IsobutylamineHCID 10340Sodium CarbonateHCID 71466451,1-Dimethylethyl N-((1S,2S)-3-chloro-2-hydroxy-1-(phenylmethyl)propyl)carbamate

Product 1

HCID 9902339tert-Butyl ((2S,3R)-3-hydroxy-4-((2-methylpropyl)amino)-1-phenylbutan-2-yl)carbamateYield 93.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
62.5 °C

Procedure

The mixture of [(1S,2S)-3-chloro-2-hydroxy-1-(phenylmethyl)propyl]carbamic acid tert-butyl ester (5, 100 g), isobutyl amine (294 g), sodium carbonate (31.3 g) and water was heated to 60-65° C. and maintained for 3 hours. After completion of reaction water (200 mL) was added and distilled out excess isobutyl amine under vacuum at below 75° C. Water (800 mL) was added to the distillate, cooled to 25-35° C. and stirred for 2 hours. The obtained solid was filtered and washed with water to get title compound 4 (yield 105 g).

Workup

  1. temperaturemaintained for 3 hours
  2. additionwas added
  3. distillationdistilled out excess isobutyl amine under vacuum at below 75° C
  4. additionWater (800 mL) was added to the distillate
  5. temperaturecooled to 25-35° C.
  6. filtrationThe obtained solid was filtered
  7. washwashed with water

Sources & evidence

ORD record
ord-1ba6c014a2cf477e94fbb9215a61c70a
Source dataset
uspto-grants-2015_12
Patent number
US09216990B2

Reaction notes

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