Benzylamine → Cbz-Trp-NHBn

HRID 2074345Notes

Reaction equation

HRID 2074345 reaction equation
[NH:1]([C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[C@H:2]([C:13]([OH:15])=O)[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[CH2:26]([NH2:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C1CCC(N=C=NC2CCCCC2)CC1>C1COCC1>[NH:1]([C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[C@H:2]([C:13]([NH:33][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:15])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 10868DicyclohexylcarbodiimideHCID 101176benzyloxycarbonyl-L-tryptophan

Product 1

HCID 16735215Cbz-Trp-NHBn

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Same procedure as above with Z-Trp-OH (2 g, 5.9 mmol), benzylamine (645 μL, 5.9 mmol), DCC (1.58 g, 7.65 mmol) and THF (88 mL). A white solid was obtained after precipitation in methanol/pentane (777 mg, 31%). 1H NMR (300 MHz, CDCl3) δ 3.18 (dd, J=14.3 Hz, J=8.1 Hz, 1H, CH2), 3.39 (dd, J=14.3 Hz, J=4.9 Hz, 1H, CH2), 4.3 (m (AB), 2H, CH2 (Bn)), 4.53 (m, 1H, CHα), 5.11 (s, 2H, CH2 (Z)), 5.52 (m, 1H, NH), 5.90 (m, 1H, NH), 6.91-7.70 (m, 15 aromatic H), 8.01 (s, 1H, NH indole). 13C NMR (75 MHz, CDCl3) δ 28.7 (CH2 Trp), 43.4 (CH2), 56.1 (CHα), 67 (CH2 (Z)), 111.2, 118.7, 119.7, 122.2, 123.2, 123.4, 127.2, 127.3, 127.6, 128, 128.2, 128.5, 136.1, 136.2, 137.5, 137.6 (20 aromatic C), 156 (CO carbamate), 171.2 (CO amide). Anal. Calcd. for C26H25N3O3, 0.75H2O: C, 70.81; H, 6.06; N, 9.53. Found: C, 70.84; H, 6.80; N, 9.21.

Workup

  1. customA white solid was obtained
  2. customafter precipitation in methanol/pentane (777 mg, 31%)

Sources & evidence

ORD record
ord-4249a670defa4a70a49de79a1c342d09
Source dataset
uspto-grants-2011_04
Patent number
US07919468B2

Reaction notes

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