Triethylamine → HCID 67121151, compound

HRID 1510448Notes

Reaction equation

HRID 1510448 reaction equation
[Cl:1][C:2]1[C:3]([C:17]([NH:19][C@@H:20]2[CH2:24][CH2:23][C@H:22]([OH:25])[CH2:21]2)=[O:18])=[N:4][O:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1.N([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])CC(O)=O.[OH2:38].ON1C2C=CC=[CH:48][C:43]=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C>O1CCCC1>[C:34]([O:33][C:31]([CH2:43][C:48]([O:25][C@H:22]1[CH2:23][CH2:24][C@@H:20]([NH:19][C:17]([C:3]2[C:2]([Cl:1])=[C:6]([C:7]3[CH:12]=[CH:11][C:10]([C:13]([F:15])([F:14])[F:16])=[CH:9][CH:8]=3)[O:5][N:4]=2)=[O:18])[CH2:21]1)=[O:38])=[O:32])([CH3:35])([CH3:36])[CH3:37]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 25181770HCID 25181770, compound

Product 1

HCID 67121151HCID 67121151, compoundYield 30.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Chloro-N-((1R,3S)-3-hydroxycyclopentyl)-5-(4-(trifluoromethyl)phenyl) isoxazole-3-carboxamide (57 mg, 152 μmol) was dissolved in tetrahydrofuran (2 mL) at room temperature and treated with Boc-Gly-OH (28 mg, 160 μmol), 1-Hydroxybenzotriazole hydrate (21 mg, 155 μmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (34 mg, 177 μmol) and triethylamine (21 μL, 151 μmol). The mixture was stirred overnight and the volatiles were then removed in vacuo. The crude residue was purified by silica gel chromatography, eluting with 55% ethylacetate in hexanes to give the title compound (1S,3R)-3-(4-chloro-5-(4-(trifluoromethyl)phenyl)isoxazole-3-carboxamido)cyclopentyl 2-(tert-butoxycarbonyl)acetate (25 mg, 47 μmol).

Workup

  1. customthe volatiles were then removed in vacuo
  2. customThe crude residue was purified by silica gel chromatography
  3. washeluting with 55% ethylacetate in hexanes

Sources & evidence

ORD record
ord-6e7431ae446843b1a81231a1af3fd1e8
Source dataset
uspto-grants-2012_07
Patent number
US08211927B2

Reaction notes

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