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Water → (2s,3s)-n-Cyclopropyl-3-(tert-butoxycarbonyl)-amino-2-hydroxyhexanoic acid amide

HRID 1928703
Notes
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Reaction equation

HRID 1928703 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[C:5]([O:9][C:10](N[C@@H](CCC)[C@H](O)C(O)=O)=[O:11])([CH3:8])([CH3:7])[CH3:6].[CH:22]1[CH:27]=[C:26]2N=N[N:30](O)[C:25]2=[CH:24][CH:23]=1.[OH2:32].CCN=C=NCCCN(C)C.Cl.C([O-])(O)=O.[Na+].[OH2:50]>C1COCC1.C(OCC)(=O)C>[CH:1]1([NH:4][C:24](=[O:50])[C@@:25]([NH2:30])([OH:32])[C@@H:26]([C:10]([O:9][C:5]([CH3:8])([CH3:7])[CH3:6])=[O:11])[CH2:27][CH2:22][CH3:23])[CH2:3][CH2:2]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 6

HCID 962WaterHCID 69828CyclopropylamineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 29928234(2S,3S)-3-tert-butoxycarbonylamino-2-hydroxyhexanoic acid

Product 1

HCID 68955931(2s,3s)-n-Cyclopropyl-3-(tert-butoxycarbonyl)-amino-2-hydroxyhexanoic acid amide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

Cyclopropylamine (13.9 g, 242.6 mmol) was dropwise added to a mixed solution of ethyl acetate (250 g)/THF (250 g)=1/1 and (2S,3S)-3-(tert-butoxycarbonyl)amino-2-hydroxyhexanoic acid (50.0 g, 202.2 mmol). The mixture was cooled by ice. A mixed solution of HOBt monohydrate (32.5, 212.3 mmol), EDC hydrochloride (42.6 g, 222.4 mmol) and water (43 g) was dropwise added thereto, and the mixture was stirred for 14 hours with cooling by ice. Next, 5% NaHCO3 aqueous solution (250 g) was added thereto, and the mixture was heated up to 40° C. Then, the aqueous layer was removed, and the organic-layer was washed twice with 5% NaHCO3 aqueous solution (250 g) at 40° C. and finally washed with water (250 g), to obtain a solution of (2S,3S)—N-cyclopropyl-3-(tert-butoxycarbonyl)-amino-2-hydroxyhexanoic acid amide (reaction yield: 95 mol %, extraction yield: 89 mol %, chemical purity: 96.9 area %).

Workup

  1. temperatureThe mixture was cooled by ice
  2. temperaturewith cooling by ice
  3. customThen, the aqueous layer was removed
  4. washthe organic-layer was washed twice with 5% NaHCO3 aqueous solution (250 g) at 40° C.
  5. washfinally washed with water (250 g)

Sources & evidence

ORD record
ord-2726c1ef860f413f90fa8707449f5771
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08183413B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes