Cyclopentanol → HCID 57971607, compound

HRID 2276952Notes

Reaction equation

HRID 2276952 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:22]1(O)[CH2:26][CH2:25][CH2:24][CH2:23]1.CN(C1C=CC=CN=1)C.Cl.CN(C)CCCN=C=NCC>CN(C=O)C.CCOC(C)=O.O>[CH:22]1([O:14][C:13](=[O:15])[C@@H:12]([NH:11][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH2:16][O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

8

Reactant 4

HCID 7298CyclopentanolHCID 218852-DimethylaminopyridineHCID 1715617Z-Ser(tBu)-OHHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 57971607HCID 57971607, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

(S)-2-Benzyloxycarbonylamino-3-tert-butoxy-propionic acid (4 g, 0.014 mol) was dissolved in DMF (40 ml). Cyclopentanol (2.54 ml, 0.027 mol) and dimethylaminopyridine (0.165 g, 0.014 mol) were added. The solution was cooled to 0° C. using an ice bath and to it was added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (2.73 g, 0.014 mol, 1.05 eq.). The mixture was stirred at 0° C. for 10 minutes and then allowed to warm to r.t. and stirred for a further 18 hours. To the reaction mixture was added water (20-30 ml) followed by EtOAc (40 ml). The layers were separated and the aqueous layer re-extracted with EtOAc (15 ml). The combined organic layers were washed with water (4×20 ml), dried (MgSO4) and the solvent removed in vacuo to give a residue. Purification by column chromatography (1:1 EtOAc/heptane) gave the product as a colourless oil (3.82 g, 78% yield). 1H NMR (300 MHz, CDCl3), δ: 1.15 (9H, s, CH3×3), 1.50-1.90 (8H, m, CH2×4), 3.57 (1H, dd, J=7.4, 1.2 Hz, CH), 3.85 (1H, dd, J=7.4, 1.2 Hz, CH), 4.45 (1H, m, CH), 5.15 (2H, s, CH2), 5.25 (1H, m, CH), 5.65 (1H, d, CH, J=7.6 Hz), 7.30-7.50 (5H, m, ArH×5).

Workup

  1. temperatureto warm to r.t.
  2. stirringstirred for a further 18 hours
  3. customThe layers were separated
  4. extractionthe aqueous layer re-extracted with EtOAc (15 ml)
  5. washThe combined organic layers were washed with water (4×20 ml)
  6. dry with materialdried (MgSO4)
  7. customthe solvent removed in vacuo
  8. customto give a residue
  9. customPurification by column chromatography (1:1 EtOAc/heptane)

Sources & evidence

ORD record
ord-fc247646ba764d29bdac15220eea23e4
Source dataset
uspto-grants-2015_09
Patent number
US09133104B2

Reaction notes

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