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1,2-Dichloroethane → N-Boc-Tyr(Bn)-Ala-Trp-NH(CH2)4NHBoc

HRID 2074359
Notes
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Reaction equation

HRID 2074359 reaction equation
[NH2:1][C@H:2]([C:13]([NH:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[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:28]([C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[C@H:29]([C:45]([NH:47][C@H:48]([C:50](O)=[O:51])[CH3:49])=[O:46])[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[CH:33][CH:32]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl.CN(C=O)C>[NH:28]([C:53]([O:55][C:56]([CH3:57])([CH3:59])[CH3:58])=[O:54])[C@H:29]([C:45]([NH:47][C@H:48]([C:50]([NH:1][C@H:2]([C:13]([NH:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[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:51])[CH3:49])=[O:46])[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[CH:33][CH:32]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 16735218Trp-NH(CH2)4NHBocHCID 57611766N-Boc-Tyr(Bn)-Ala-OH

Product 1

HCID 16735462N-Boc-Tyr(Bn)-Ala-Trp-NH(CH2)4NHBoc

Reagents, catalysts & solvents 1

HCID 22350042
dichloromethane N,N-dimethylformamide
Solvent

Procedure

compound SP305R. Same procedure as above with Trp-NH(CH2)4NHBoc (204.6 mg, 0.546 mmol), N-Boc-Tyr(Bn)-Ala-OH (242 mg, 0.546 mmol), EDC (116 mg, 0.61 mmol) and HOBt (82.2 mg, 0.61 mmol) in CH2Cl2/DMF (2.2 mL, 1/1). The crude tripeptide (282 mg) can be recrystallized from hot THF to give a white solid as an analytical sample (89.1 mg, 31.5%). 1H NMR (300 MHz, DMSO-d6) δ 1.18-1.4 (m, 7H, 2 CH2 putrescine, CH3), 1.28 (s, 9H, (CH3)3), 1.37 (s, 9H, (CH3)3), 2.61 (m, 1H, CH2 Tyr or Trp), 2.85-3.1 (m, 7H, CH2 Tyr, CH2 Trp, 2 CH2 putrescine), 4.08 (m, 1H, CHα), 4.29 (m, 1H, CHα), 4.45 (m, 1H, CHα), 5.03 (s, 2H, CH2 (Bn)), 6.73 (m, 1H), 6.87-7.43 (m, 14 aromatic H), 7.56 (d, J=7.7 Hz, 1H), 7.83 (m, 1H), 7.99 (m, 2H), 10.8 (s, 1NH). 13C NMR (75 MHz, DMSO-d6) δ 18.2 (CH3), 26.2, 26.8 (2 CH2 putrescine), 28.1 (CH2 Trp), 28.2 ((CH3)3), 36.3 (CH2 Tyr), 38.2, 39.2 (2 CH2 putrescine), 48.2, 53.4, 55.8 (CHα Ala, Tyr, Trp), 69 (CH2 (Bn)), 77.3, 78 (2 C(CH3)3), 109.8, 111.1, 114.2, 118.1, 118.4, 120.7, 123.4, 127.3, 127.5, 127.7, 128.3, 130.1, 130.3, 136, 137.2 (19 aromatic C), 155.2, 155.5, 156.8 (Car-O, 2 CO carbamate), 170.7, 171.4, 171.8 (3 CO amide). Anal. Calcd. for C44H58N6O8: C, 66.14; H, 7.32; N, 10.52. Found: C, 65.89; H, 7.34; N, 10.77.

Workup

  1. customThe crude tripeptide (282 mg) can be recrystallized from hot THF
  2. customto give a white solid as an analytical sample (89.1 mg, 31.5%)

Sources & evidence

ORD record
ord-1ba4432e3ccf415ba7d6583afd78c202
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