Ammonium Hydroxide → HCID 71715230, compound

HRID 1527940Notes

Reaction equation

HRID 1527940 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:9][C@H:8]([NH:10][C:11]([C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]=2[OH:23])=[O:12])[CH2:7][N:6]1[CH2:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)=O.[OH-].[NH4+:32]>O1CCCC1>[CH:25]1([CH2:24][N:6]2[CH2:7][C@@H:8]([NH:10][C:11]([C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:14]=3[OH:23])=[O:12])[CH2:9][C@H:5]2[C:3]([NH2:32])=[O:2])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 71715056HCID 71715056, compound

Product 1

HCID 71715230HCID 71715230, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of (2S,4S)-1-cyclohexylmethyl-4-[(1-hydroxy-naphthalene-2-carbonyl)-amino]-pyrrolidine-2-carboxylic acid methyl ester (50 mg) in tetrahydrofuran (7 mL), aq. ammonium hydroxide (15 mL) was added in a seal tube and the mixture was heated for 24 hrs at 95° C. The reaction mixture was concentrated and the aqueous layer was extracted with diethyl ether, washed with brine, dried, concentrated and was purified by column chromatography to obtain (2S,4S)-1-cyclohexylmethyl-4-[(1-hydroxy-naphthalene-2-carbonyl)-amino]-pyrrolidine-2-carboxylic acid amide (8 mg, 16% yield) as a light brown solid. MS calcd. for C23H30N3O3 [(M+H)+] 396, obsd. 396.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionthe aqueous layer was extracted with diethyl ether
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-85d06fb1353d4df782c4191585644100
Source dataset
uspto-grants-2015_07
Patent number
US09090559B2

Reaction notes

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