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1-Hydroxybenzotriazole → trans-4-(3-Biphenyloxy) N-tert-butoxycarbonyl-L-proline 2-(N-tert-butoxycarbonylamino)ethylamide

HRID 2185491
Notes
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Reaction equation

HRID 2185491 reaction equation
ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[C:23]1([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH:28]=[CH:27][CH:26]=[C:25]([O:29][C@H:30]2[CH2:34][N:33]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C@H:32]([C:42](O)=[O:43])[CH2:31]2)[CH:24]=1.[NH2:51][CH2:52][CH2:53][NH:54][C:55](=[O:61])[O:56][C:57]([CH3:60])([CH3:59])[CH3:58]>ClCCl.C(Cl)(Cl)Cl.C(N(CC)CC)C>[C:57]([O:56][C:55]([NH:54][CH2:53][CH2:52][NH:51][C:42](=[O:43])[C@@H:32]1[CH2:31][C@@H:30]([O:29][C:25]2[CH:24]=[C:23]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[CH:28]=[CH:27][CH:26]=2)[CH2:34][N:33]1[C:35]([O:37][C:38]([CH3:40])([CH3:41])[CH3:39])=[O:36])=[O:61])([CH3:60])([CH3:59])[CH3:58]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 187201N-BOC-ethylenediamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21341574HCID 21341574, compound

Product 1

HCID 54515339trans-4-(3-Biphenyloxy) N-tert-butoxycarbonyl-L-proline 2-(N-tert-butoxycarbonylamino)ethylamide
Yield 90.5%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Triethylamine (56 μL), 1-hydroxybenzotriazole (25 mg), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (78 mg) were added to a solution of trans-4-(3-biphenyloxy)-N-tert-butoxycarbonyl-L-proline (B), (141 mg) and tert-butyl N-(2-aminoethyl)carbamate (65 mg) in dichloromethane (3 mL). After stirring at room temperature overnight, the reaction mixture was diluted with chloroform and washed with saturated sodium hydrogen carbonate and brine. The organic layer was dried over anhydrous sodium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography chloroform:methanol=100:1, v/v to give the titled compound (175 mg) as a colorless foam: 1H NMR (400 MHz, CDCl3) δ 1.45 (s, 9H), 2.37 (m, 1H), 2.59 (m, 1H), 3.28 (m, 1H), 3.29 (s, 2H), 3.40 (m, 1H), 3.73 (m, 2H), 4.41 (m, 1H), 5.01 (m, 1H), 5.18 (m, 1H), 6.86 (m, 2H), 7.08 (s, 1H), 7.20 (d, J=7.3 Hz, 1H), 7.35 (t, J=7.3 E4z, 2H), 7.43 (t, J=7.3 Hz, 2H), and 7.56 (d, J=7.3 Hz,2H).

Workup

  1. washwashed with saturated sodium hydrogen carbonate and brine
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customevaporated in vacuo
  4. customThe residue was purified by silica gel column chromatography chloroform

Sources & evidence

ORD record
ord-c1cc5ff03e9f4460b2f598301780fada
Source dataset
uspto-grants-2002_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06399629B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes