Hydrochloric Acid → 3-{[({(1R,2S)-2-[(tert-butoxycarbonyl)amino]cyclopentyl}carbonyl)amino]sulfonyl}propylacetic acid

HRID 1662068Notes

Reaction equation

HRID 1662068 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[C:14]([OH:16])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:17][S:18]([CH2:21][CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])(=[O:20])=[O:19].C1N=CN(C(N2C=NC=C2)=O)C=1.C1CCN2C(=NCCC2)CC1.Cl>C(OCC)(=O)C.CN(C=O)C>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[C:14]([NH:17][S:18]([CH2:21][CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])(=[O:19])=[O:20])=[O:16])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 1268160(1R,2S)-2-(tert-Butoxycarbonylamino)cyclopentanecarboxylic acidHCID 571720245-Sulfamoylpentanoic acid

Product 1

HCID 674291603-{[({(1R,2S)-2-[(tert-butoxycarbonyl)amino]cyclopentyl}carbonyl)amino]sulfonyl}propylacetic acid

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (1R,2S)-2-[(tert-butoxycarbonyl)amino]cyclopentanecarboxylic acid (1.0 g), DMF (10 ml), 3-(aminosulfonyl)propylacetic acid (0.95 ml), CDI(0.85 g), and DBU (0.80 g) was stirred at room temperature for 3 days. To the reaction mixture were added 1 M hydrochloric acid and ethyl acetate, and the organic layer was separated. The organic layer was washed with a saturated sodium bicarbonate solution, then dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 3-{[({(1R,2S)-2-[(tert-butoxycarbonyl)amino]cyclopentyl}carbonyl)amino]sulfonyl}propylacetic acid (1.2 g).

Workup

  1. customthe organic layer was separated
  2. washThe organic layer was washed with a saturated sodium bicarbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bb5c414b732946879f0544db0e3c03ae
Source dataset
uspto-grants-2011_10
Patent number
US08030489B2

Reaction notes

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