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

HRID 2074357
Notes
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Reaction equation

HRID 2074357 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:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[C@H:24]([C:40]([NH:42][C@H:43]([C:48](O)=[O:49])[CH2:44][C:45](=[O:47])[NH2:46])=[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:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[C@H:24]([C:40]([NH:42][C@H:43]([C:48]([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:49])[CH2:44][C:45](=[O:47])[NH2:46])=[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 57611773N-Boc-Tyr(Bn)-Asn-OH

Product 1

HCID 16737396N-Boc-Tyr(Bn)-Asn-Trp-NHCH2PhYield 48%

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

compound A416. Same procedure as above with Trp-NHCH2Ph (63.03 mg, 0.215 mmol), N-Boc-Tyr(Bn)-Asn-OH (105.0 mg, 0.216 mmol), EDC (44 mg, 0.226 mmol) and HOBt (31 mg, 0.226 mmol) in CH2Cl2/DMF (1.5 mL/1.5 mL). After treatment, the crude residue was triturated with CH2Cl2/pentane to afford a white solid (78 mg, 48%). 1H NMR (300 MHz, DMSO-d6) δ 1H NMR (300 MHz, DMSO-d6) δ 1.29 (s, 9H, (CH3)3), 2.30-3.26 (m, 6H, CH2 Tyr, CH2 Trp, CH2 Asn), 4.08 (m, 1H, CHα), 4.24 (s, 2H, NCH2Ph), 4.49 (m, 1H, CHα), 4.56 (m, 1H, CHα), 5.03 (broad s, 2H, OCH2Ph), 6.88-7.56 (m, 17H), 8.17 (d, J=8 Hz, 1H, NH), 8.23 (d, J=8 Hz, 1H, NH), 8.51 (t, J=6 Hz, 1H, NH), 10.84 (s, 1H, NH). 13C NMR (75 MHz, CD3OD) δ 28.5 (CH2 Trp), 28.6 ((CH3)3), 37.3, 38.1 (CH2 Tyr, CH2 Asn), 44.1 (NCH2Ph), 51.7, 55.9, 57.6 (CHα Tyr, Asn, Trp), 71.0 (OCH2Ph), 80.9 (C Boc), 110.9 (C), 112.4, 115.9, 116.0, 119.4, 119.9, 122.5, 124.8, 128.0, 128.5, 128.6, 128.8, 129.4, 129.5, 130.6 (C), 131.4 (CH), 138.0, 138.8, 139.5 (aromatic C), 157.9, 159.1 (aromatic C and CO Boc), 172.7, 173.6, 174.4, 174.9 (CO amide).

Workup

  1. customAfter treatment, the crude residue was triturated with CH2Cl2/pentane

Sources & evidence

ORD record
ord-86d09d1f2cb74c81831d84afdbb4fbce
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