3-Pyridinemethanamine → 2(S),5(S)-Bis-(N-(3-pyridylmethylamino-carbonyl)-amino)-1,6-diphenyl-3(S)-hydroxyhexane

HRID 742918Notes

Reaction equation

HRID 742918 reaction equation
[N+](C1C=CC(O[C:9]([NH:11][C@H:12]([C@@H:20]([O:43][Si](C)(C)C)[CH2:21][C@@H:22]([NH:30][C:31]([O:33]C2C=CC([N+]([O-])=O)=CC=2)=O)[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:10])=CC=1)([O-])=O.[NH2:50][CH2:51][C:52]1[CH:53]=[N:54][CH:55]=[CH:56][CH:57]=1>CN(C=O)C>[N:54]1[CH:55]=[CH:56][CH:57]=[C:52]([CH2:51][NH:50][C:9]([NH:11][C@H:12]([C@@H:20]([OH:43])[CH2:21][C@@H:22]([NH:30][C:31]([NH:50][CH2:51][C:52]2[CH:53]=[N:54][CH:55]=[CH:56][CH:57]=2)=[O:33])[CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:10])[CH:53]=1

Participants

4

Reactant 2

HCID 310183-PyridinemethanamineHCID 186556462(S),5(S)-Bis-(N-(p-nitrophenoxycarbonyl)-amino)-1,6-diphenyl-3(S)-trimethylsiloxy-hexane

Product 1

HCID 542471732(S),5(S)-Bis-(N-(3-pyridylmethylamino-carbonyl)-amino)-1,6-diphenyl-3(S)-hydroxyhexane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 87 mg of the resultant compound from Example 218 in 1 ml of DMF was added 0.028 ml of 3-aminomethylpyridine. After 18 hours, the solvent was removed in vacuo and the residue was dissolved in 1 ml of methanol and 0.05 ml of chlorotrimethylsilane was added. After 0.5 hour, the solvent was removed in vacuo, neutralized with sodium bicarbonate solution and extraction with ethyl acetate (2×25 ml). The organic solution was dried and concentrated. Purification by silica gel column chromotography provided 35 mg of desired product. 1H NMR (CD3OD): δ1.60 (t, 2H), 2.60-2.80 (m, 4H), 3.70 (m, 1H), 4.00 (m, 1H), 4.10 (m, 1H), 4.25-4.35 (m, 4H), 7.10-7.25 (m, 10H), 7.35 (m, 2H), 7.60 (m, 2H), 8.40 (m, 4H). Mass spectrum: (M+H)+ =553.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in 1 ml of methanol
  3. addition0.05 ml of chlorotrimethylsilane was added
  4. waitAfter 0.5 hour
  5. customthe solvent was removed in vacuo
  6. extractionneutralized with sodium bicarbonate solution and extraction with ethyl acetate (2×25 ml)
  7. customThe organic solution was dried
  8. concentrationconcentrated
  9. customPurification by silica gel column chromotography

Sources & evidence

ORD record
ord-b811d7b9372f4acb9d8bd9b6e1b993cc
Source dataset
uspto-grants-1996_09
Patent number
US05554783

Reaction notes

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