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1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 3(S)-(tert-butoxyformamido)-2(S)-hydroxy-N-(1(S)-phenylpropyl)heptanamide

HRID 635638
Notes
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Reaction equation

HRID 635638 reaction equation
O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[C:24]1([C@@H:30]([NH2:33])[CH2:31][CH3:32])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[C:34]([O:38][C:39]([NH:41][C@@H:42]([CH2:48][CH2:49][CH2:50][CH3:51])[C@H:43]([OH:47])[C:44](O)=[O:45])=[O:40])([CH3:37])([CH3:36])[CH3:35]>ClCCl>[C:34]([O:38][C:39]([NH:41][C@@H:42]([CH2:48][CH2:49][CH2:50][CH3:51])[C@H:43]([OH:47])[C:44]([NH:33][C@H:30]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:31][CH3:32])=[O:45])=[O:40])([CH3:37])([CH3:36])[CH3:35]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 6993773(1S)-1-phenylpropan-1-amineHCID 206399783(S)-(tert-butoxyformamido)-2(S)-hydroxyheptanoic acid

Product 1

HCID 206399793(S)-(tert-butoxyformamido)-2(S)-hydroxy-N-(1(S)-phenylpropyl)heptanamide
Yield 75.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

229 mg of 1-hydroxybenzotriazole monohydrate, 287 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 148 mg of (S)-(−)-1-phenylpropylamine were added in sequence to a solution of 260 mg of 3(S)-(tert-butoxyformamido)-2(S)-hydroxyheptanoic acid in 10 ml of dichloromethane. The mixture was stirred at room temperature for 3 hours, then diluted with dichloromethane and washed in sequence with 5% citric acid solution, saturated sodium bicarbonate solution and saturated brine. The organic phase was dried over anhydrous magnesium sulphate and the solvent was evaporated to give 285 mg of 3(S)-(tert-butoxyformamido)-2(S)-hydroxy-N-(1(S)-phenylpropyl)heptanamide, MS: m/e 379.1 [M+H]+.

Workup

  1. washwashed in sequence with 5% citric acid solution, saturated sodium bicarbonate solution and saturated brine
  2. dry with materialThe organic phase was dried over anhydrous magnesium sulphate
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-b33c2eb908984462bba04a4ce2e61113
Source dataset
uspto-grants-2001_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06187905B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes