Ammonia → HCID 178453950, compound

HRID 1437322Notes

Reaction equation

HRID 1437322 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]([OH:17])=O)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C(=O)[N:22](O)C(=O)C1.C1(N=C=NC2CCCCC2)CCCCC1.N>C(OCC)(=O)C.O1CCCC1.O>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15](=[O:17])[NH2:22])[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 178453972HCID 178453972, compound

Product 1

HCID 178453950HCID 178453950, compoundYield 76%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of trans-4-tert-butoxycarbonylamino-cyclohexanecarboxylic acid (15 g, 61.7 mmol) and 1-hydroxysuccinimide (76 g, 61.7 mmol) in ethyl acetate (200 ml) was treated with a solution of dicyclohexylcarbodiimide (12.7 g, 61.7 mmol) in ethyl acetate (50 ml). After stirring overnight the mixture was filtered and evaporated affording a yellow solid. This was redissolved in tetrahydrofuran (300 ml) and treated gaseous ammonia was bubbled through the solution for 15 minutes. Filtration afforded a white solid which was stirred in water (200 ml) for 1 hour. Filtration and drying afforded a white solid (11.3 g, 76%).

Workup

  1. filtrationwas filtered
  2. customevaporated
  3. customaffording a yellow solid
  4. customwas bubbled through the solution for 15 minutes
  5. filtrationFiltration
  6. customafforded a white solid which
  7. filtrationFiltration
  8. customdrying

Sources & evidence

ORD record
ord-a7aa904ccf2a40b48c05c29988dde6b4
Source dataset
uspto-grants-2009_11
Patent number
US07622481B2

Reaction notes

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