Water → HCID 178521676, compound

HRID 1444656Notes

Reaction equation

HRID 1444656 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C@@H:7]2[CH2:12][CH2:11][C@H:10]([NH2:13])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[C:16]12([N:26]=[C:27]=[O:28])[CH2:25][CH:20]3[CH2:21][CH:22]([CH2:24][CH:18]([CH2:19]3)[CH2:17]1)[CH2:23]2.C(N(CC)CC)C.O>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C@@H:7]2[CH2:8][CH2:9][C@H:10]([NH:13][C:27]([NH:26][C:16]34[CH2:25][CH:20]5[CH2:19][CH:18]([CH2:24][CH:22]([CH2:21]5)[CH2:23]3)[CH2:17]4)=[O:28])[CH2:11][CH2:12]2)=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 20599951-IsocyanatoadamantaneHCID 178511705HCID 178511705, compound

Product 1

HCID 178521676HCID 178521676, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution compound 10 in DMF was added 1-adamantyl isocyanate (0.16 g, 0.91 mmol) followed by triethylamine (0.10 g, 1.0 mmol) at 0° C. The reaction mixture was stirred overnight. The reaction mixture was poured into water, and the resulting precipitates were collected and washed with water. The crude product was recrystallized from DCM/hexanes. Yield: 0.31 g (88% of theory). M.P.: 207° C. 1H NMR (300 MHz, CDCl3): δ 6.98-6.91 (m, 2H), 6.84-6.78 (m, 2H), 4.34 (s, 1H), 4.30 (d, J=9.8 Hz, 1H), 4.20 (s, 1H), 3.71-3.56 (m, 1H), 2.13-1.44 (m, 23H).

Workup

  1. customthe resulting precipitates
  2. customwere collected
  3. washwashed with water
  4. customThe crude product was recrystallized from DCM/hexanes

Sources & evidence

ORD record
ord-90f4b951fa32463f9f2b6ae45f15890e
Source dataset
uspto-grants-2010_02
Patent number
US07662910B2

Reaction notes

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