Diethyl Ether → 5-(2-Oxohexahydrothieno[3,4-d]imidazol-4-yl)-pentanoic acid (4-amino-cyclohexyl)amide

HRID 59019

Reaction equation

HRID 59019 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH:5]([NH2:8])[CH2:4][CH2:3]1.C1C(=O)N([O:16][C:17]([CH2:19][CH2:20][CH2:21][CH2:22][CH:23]2[S:27][CH2:26][CH:25]3[NH:28][C:29]([NH:31][CH:24]23)=[O:30])=O)C(=O)C1.CCOCC>CN(C=O)C>[NH2:1][CH:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:17](=[O:16])[CH2:19][CH2:20][CH2:21][CH2:22][CH:23]2[CH:24]3[CH:25]([NH:28][C:29](=[O:30])[NH:31]3)[CH2:26][S:27]2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 183741,4-DiaminocyclohexaneHCID 434213NHS-Biotin

Product 1

HCID 911075615-(2-Oxohexahydrothieno[3,4-d]imidazol-4-yl)-pentanoic acid (4-amino-cyclohexyl)amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1,4-Diaminocyclohexane (37.6 mg, 0.33 mmol) was dissolved in dry DMF (3 mL) under nitrogen. Solution of NHS-Biotin (102.3 mg, 0.3 mmol) in dry DMF (3 mL) was added to stirred solution of diamine over a 15 min period. Reaction mixture was stirred for 16 h at ambient temperature. Dilution of reaction mixture with dry Et2O (50 mL) produced white precipitate. Precipitated 19b was filtered, washed with EtOAc (3×20 mL) for removing of NHS and dried in high vacuum.

Workup

  1. customReaction mixture
  2. customproduced white precipitate
  3. customPrecipitated 19b
  4. filtrationwas filtered
  5. washwashed with EtOAc (3×20 mL)
  6. customfor removing of NHS
  7. customdried in high vacuum

Sources & evidence

ORD record
ord-2d2265e01eef45f488c6e4e5b7242d95
Source dataset
uspto-grants-2016_09
Patent number
US09439877B2

Linked notes

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