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

HRID 2074358Notes

Reaction equation

HRID 2074358 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:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[C@H:24]([C:40]([NH:42][CH2:43][C:44](O)=[O:45])=[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:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[C@H:24]([C:40]([NH:42][CH2:43][C:44]([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:45])=[O:41])[CH2:25][C:26]1[CH:27]=[CH:28][C:29]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 775625(S)-2-Amino-N-benzyl-3-(1H-indol-3-yl)propanamideHCID 11102023N-Boc-Tyr(Bn)-Gly-OH

Product 1

HCID 16737177N-Boc-Tyr(Bn)-Gly-Trp-NHCH2Ph

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

compound PSV11R. Same procedure as above with Trp-NHCH2Ph (82.43 mg, 0.281 mmol), N-Boc-Tyr(Bn)-Gly-OH (109.26 mg, 0.255 mmol), EDC (53.87 mg, 0.281 mmol) and HOBt (37.97 mg, 0.281 mmol) in CH2Cl2/DMF (2 mL/0.8 mL). The crude residue was triturated with CH2Cl2/pentane to afford a white solid (113.76, 63%). mp 183° C. 1H NMR (300 MHz, CDCl3) δ 1.38 (s, 9H, (CH3)3), 2.81 (m, 2H, CH2 Tyr), 3.26 (m, 2H), 3.72 (m, 2H, CH2 Gly), 4.30 (m, 3H, CHα and CH2Bn), 4.80 (m, 1H, CHα), 5.0 (broad s, 3H, NHBoc and CH2O), 6.72 (m, 1H, NH Gly), 6.90-7.40 (m, 20H, aromatic H and NH), 7.63 (d, 1H, J=7 Hz), 8.35 (s, 1H, NH indole). 13C NMR (75 MHz, CDCl3) δ 28.3 (CH2 Trp and (CH3)3), 37.5 (CH2 Tyr), 43.1, 43.5 (CH2 (Bn), CH2 Gly), 54.0, 55.8 (CHα Tyr, Trp), 70.0 (CH2 (Bn)), 80.4 (C(CH3)3), 110.2, 111.3, 114.9, 118.7, 119.5, 122.0, 123.4, 127.2, 127.4, 127.5, 127.7, 128.0, 128.5, 128.6, 128.7, 130.3, 136.1, 137.0, 137.9 (20 aromatic C), 155.7, 157.7 (Car-O, CO carbamate), 168.9, 171.4, 172.5 (3 CO amide). Anal. Calcd. for C41H45N5O6, 1H2O: C, 68.22; H, 6.56; N, 9.71. Found: C, 68.50; H, 6.48; N, 9.98.

Workup

  1. customThe crude residue was triturated with CH2Cl2/pentane
  2. customto afford a white solid (113.76, 63%)

Sources & evidence

ORD record
ord-e490815854ef4563b71b3d17167859eb
Source dataset
uspto-grants-2011_04
Patent number
US07919468B2

Reaction notes

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