Piperidine → HCID 15431840, compound

HRID 2237361Notes

Reaction equation

HRID 2237361 reaction equation
[NH2:1][C@H:2]([C:4]([NH:6][C@H:7]([C:15]([NH:17][C@H:18]([C:23]([N:25]1[CH2:37][CH2:36][CH2:35][C@H:26]1[C:27]([NH:29][C@H:30]([C:32]([OH:34])=[O:33])[CH3:31])=[O:28])=[O:24])[CH2:19][CH:20]([CH3:22])[CH3:21])=[O:16])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])[CH3:3].C[C@H](NC(OCC1[C:59]2[C:54](=CC=CC=2)C2C1=CC=CC=2)=O)C=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.N1CCCCC1.[N+](C1C=CC=CC=1[S:99](Cl)(=O)=O)([O-])=O.CCN(C(C)C)C(C)C.CC1C=CC(CSCCO)=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>CN(C=O)C.C(Cl)Cl>[SH:99][CH2:59][CH2:54][NH:1][C@H:2]([C:4]([NH:6][C@H:7]([C:15]([NH:17][C@H:18]([C:23]([N:25]1[CH2:37][CH2:36][CH2:35][C@H:26]1[C:27]([NH:29][C@H:30]([C:32]([OH:34])=[O:33])[CH3:31])=[O:28])=[O:24])[CH2:19][CH:20]([CH3:22])[CH3:21])=[O:16])[CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:5])[CH3:3]

Participants

12

Reactant 9

HCID 8082PiperidineHCID 11776TriphenylphosphineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 5462977Diethyl azodicarboxylateHCID 10017393HCID 10017393, compoundHCID 15431836HCID 15431836, compoundHCID 154318392-{[(4-Methylphenyl)methyl]sulfanyl}ethan-1-ol

Product 1

HCID 15431840HCID 15431840, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

Ala-Phe-Leu-Pro-Ala-WANG resin (SEQ ID NO:5) was prepared starting from Fmoc-Ala-WANG resin (0.44 mmol/gram) using standard Fmoc-SPPS protocols, with HBTU coupling and piperidine deprotection as described in Example 1. To 500 mg of this resin, a solution of 300 mg o-nitrobenzenesulfonylchloride in DMF (4 mL) containing DIEA (200 μL) was added. After 30 minutes, the resin was drained and washed with DMF (3×). The resin was mixed with a solution of S-(p-methylbenzyl)-2-mercaptoethanol (270 mg, 1.5 mmol) in DCM (5 mL). Triphenylphosphine (393 mg, 1.5 mmol) and diethylazodicarboxylate (DEAD, 261 mg, 1.5 mmol) were premixed in DCM (5 mL). After 1 minute, the solution was added to the resin and the reaction left for 30 minutes. The resin was washed with DCM (3×) and DMF (3×). The resin was further treated with a solution of NaSPhe (200 mg, 1.5 mmol) in DMF (4 mL) for 30 minutes. The resin was washed with DMF (3×) and MeOH/DCM (3×) and air dried.

Workup

  1. custom5) was prepared
  2. additionwas added
  3. washwashed with DMF (3×)
  4. waitAfter 1 minute
  5. additionthe solution was added to the resin
  6. waitthe reaction left for 30 minutes
  7. washThe resin was washed with DCM (3×) and DMF (3×)
  8. additionThe resin was further treated with a solution of NaSPhe (200 mg, 1.5 mmol) in DMF (4 mL) for 30 minutes
  9. washThe resin was washed with DMF (3×) and MeOH/DCM (3×) and air
  10. customdried

Sources & evidence

ORD record
ord-f8796383bc82445c996a8e2c84e5bdc2
Source dataset
uspto-grants-2010_05
Patent number
US07718598B1

Reaction notes

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