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1,2-Dichloroethane → N-Boc-Tyr(Bn)-Lys(Boc)-Trp-NHCH2Ph

HRID 2074356
Notes
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Reaction equation

HRID 2074356 reaction equation
[NH2:1][C@H:2]([C:13]([NH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[NH:23]([C:59]([O:61][C:62]([CH3:65])([CH3:64])[CH3:63])=[O:60])[C@H:24]([C:40]([NH:42][C@H:43]([C:56](O)=[O:57])[CH2:44][CH2:45][CH2:46][CH2:47][NH:48][C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])=[O:41])[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:28][CH:27]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl.CN(C=O)C>[NH:23]([C:59]([O:61][C:62]([CH3:65])([CH3:64])[CH3:63])=[O:60])[C@H:24]([C:40]([NH:42][C@H:43]([C:56]([NH:1][C@H:2]([C:13]([NH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1)=[O:57])[CH2:44][CH2:45][CH2:46][CH2:47][NH:48][C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])=[O:41])[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:28][CH:27]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 775625(S)-2-Amino-N-benzyl-3-(1H-indol-3-yl)propanamideHCID 57611779N-Boc-Tyr(Bn)-Lys(Boc)-OH

Product 1

HCID 16737397N-Boc-Tyr(Bn)-Lys(Boc)-Trp-NHCH2PhYield 67.6%

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

compound SP307P. Same procedure as above with Trp-NHCH2Ph (120.7 mg, 0.411 mmol), N-Boc-Tyr(Bn)-Lys(Boc)-OH (246.9 mg, 0.411 mmol), EDC (87.1 mg, 0.45 mmol) and HOBt (62.1 mg, 0.46 mmol) in CH2Cl2/DMF (1.8 mL, 1/1). The crude residue was triturated with MeOH/pentane to afford a white solid (243 mg, 67%). 1H NMR (300 MHz, DMSO-d6) δ 1.2-1.61 (m, 6H, 3 CH2 Lys), 1.29 (s, 9H, (CH3)3), 1.36 (s, 9H, (CH3)3), 2.64 (m, 1H, CH2 Tyr), 2.86 (m, 3H, CH2 Lys, CH2 Tyr), 3 (dd, J=14.1 Hz, J=7 Hz, 1H, CH2 Trp), 3.14 (dd, J=14.1 Hz, J=6 Hz, 1H, CH2 Trp), 4.11 (m, 1H, CHα), 4.26 (m, 3H, CH2 (Bn Trp), CHα), 4.59 (m, 1H, CHα), 5.02 (broad s, 2H, CH2 (Bn)), 6.72 (m, 1H), 6.85-7.4 (m, 19H), 7.59 (d, J=7.6 Hz, 1H), 7.89 (d, J=7.4 Hz, 1H), 8.1 (d, J=7.4 Hz, 1H), 8.38 (m, 1H), 10.8 (s, 1H). 13C NMR (75 MHz, DMSO-d6) δ 22.4, 29.2, 32 (3 CH2 Lys), 27.8 (CH2 Trp), 28.1, 28.2 (2 (CH3)3), 36.3 (CH2 Tyr), 39.8 (CH2 Lys), 42 (CH2 (Bn) Trp), 52.4, 53.5, 55.8 (CHα Tyr, Lys, Trp), 69.1 (CH2 (Bn)), 77.3, 78 (2 C(CH3)3), 109.7, 111.2, 114.3, 118.2, 118.4, 120.8, 123.5, 126.5, 126.9, 127.3, 127.5, 127.7, 128, 128.3, 130.1, 130.2, 136, 137.2, 139 (25 aromatic C), 155.2, 155.5, 156.8 (Car-O, 2 CO carbamate), 171, 171.3, 171.6 (3 CO amide). Anal. Calcd. for C50H62N6O, 2H2O: C, 65.91; H, 7.30; N, 9.22. Found: C, 65.59; H, 7.06; N, 9.09.

Workup

  1. customThe crude residue was triturated with MeOH/pentane

Sources & evidence

ORD record
ord-8245ff73b795438c94c93567ad8f052b
Source dataset
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07919468B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes