Water → (2S)-cyclopentyl[({[(1R,2R)-2-(pent-4-yn-1-yl)cyclopropyl]oxy}carbonyl)amino]ethanoic acid

HRID 522362

Reaction equation

HRID 522362 reaction equation
[CH2:1]([C@@H:6]1[CH2:8][C@H:7]1[O:9][C:10]([O:12]N1C(=O)CCC1=O)=O)[CH2:2][CH2:3][C:4]#[CH:5].[NH2:20][C@@H:21]([CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27]C1)[C:22]([OH:24])=[O:23].C(N(CC)CC)C.O>C(#N)C.C(OCC)(=O)C>[CH:25]1([C@H:21]([NH:20][C:10]([O:9][C@@H:7]2[CH2:8][C@H:6]2[CH2:1][CH2:2][CH2:3][C:4]#[CH:5])=[O:12])[C:22]([OH:24])=[O:23])[CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 736848(alphaS)-alpha-Aminocyclohexaneacetic acidHCID 895908351-[({[(1R,2R)-2-(pent-4-yn-1-yl)cyclopropyl]oxy}carbonyl)oxy]pyrrolidine-2,5-dione

Product 1

HCID 89590843(2S)-cyclopentyl[({[(1R,2R)-2-(pent-4-yn-1-yl)cyclopropyl]oxy}carbonyl)amino]ethanoic acidYield 100.9%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the product of Step 1 (457 mg) in acetonitrile (6 ml) was added (2S)-amino(cyclohexyl)ethanoic acid (352 mg) followed by triethylamine (0.720 ml) and water (6.00 ml). The mixture was stirred at room temperature for 18 hours. The mixture was diluted with ethyl acetate and washed with HCl 1N, water and brine. The organic layer was dried over sodium sulfate, filtered and concentrated. This provided the desired product (510 mg) as an oil. LRMS (ES+) M/Z (M+H)+ 308.2.

Workup

  1. washwashed with HCl 1N, water and brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fac0f28567ba41b0ab7b91c86f3a0bfb
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Linked notes

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