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Trityl chloride → HCID 72698639, compound

HRID 1482231
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Reaction equation

HRID 1482231 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@@H:19]([CH2:23][C:24]3[NH:28][N:27]=[N:26][N:25]=3)[C:20]([OH:22])=[O:21])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C(N(CC)C(C)C)(C)C.[C:38](Cl)([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>O1CCCC1>[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@@H:19]([CH2:23][C:24]3[N:28]([C:38]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)([C:51]4[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=4)[C:45]4[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=4)[N:27]=[N:26][N:25]=3)[C:20]([OH:22])=[O:21])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@@H:19]([CH2:23][C:24]3[N:25]=[N:26][N:27]([C:38]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)([C:51]4[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=4)[C:45]4[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=4)[N:28]=3)[C:20]([OH:22])=[O:21])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6456Trityl chlorideHCID 81531DiisopropylethylamineHCID 71744314(2S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(1H-1,2,3,4-tetrazol-5-yl)propanoic acidHCID 178523879HCID 178523879, compound

Product 2

HCID 72698639HCID 72698639, compound
HCID 117735885
HCID 117735885, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(2S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-(1H-tetrazol-5-yl)propanoic acid and (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(2H-tetrazol-5-yl)propanoic acid (Compound SP410, Fmoc-Ala(5-Tet)-OH) (900 mg, 2.37 mmol) were dissolved in tetrahydrofuran (2.7 ml), N,N-diisopropylethylamine (0.36 mL, 2.61 mmol) was added and the mixture was stirred for 5 minutes. A solution of trityl chloride (628 mg, 2.25 mmol) dissolved in tetrahydrofuran (0.6 ml) was added to the aforementioned reaction solution, and the mixture was stirred for 90 minutes. The reaction solution was filtered, and the collected reaction solution was concentrated under reduced pressure, and the residue was purified by reverse-phase silica gel column chromatography (10 mM aqueous ammonium acetate solution/methanol) to afford (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(1-trityltetrazol-5-yl)propanoic acid and (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(2-trityltetrazol-5-yl)propanoic acid (Compound SP409, Fmoc-Ala(5-Tet(Trt))-C)H) (644 mg, 44%).

Workup

  1. additionwas added to the aforementioned reaction solution
  2. stirringthe mixture was stirred for 90 minutes
  3. filtrationThe reaction solution was filtered
  4. customthe collected reaction solution
  5. concentrationwas concentrated under reduced pressure
  6. customthe residue was purified by reverse-phase silica gel column chromatography (10 mM aqueous ammonium acetate solution/methanol)

Sources & evidence

ORD record
ord-68109aa1c2c4496594605ab2a37b8a71
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09409952B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes