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Water → tert. Butyl (3SR,4SR)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-hydroxy-pyrrolidine-1-carboxylate

HRID 1875329
Notes
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Reaction equation

HRID 1875329 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[NH2:32][CH:33]1[CH:37]([OH:38])[CH2:36][N:35]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:34]1.O>C(Cl)Cl>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:32][CH:33]2[CH:37]([OH:38])[CH2:36][N:35]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:34]2)=[O:9])=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 950485-Chloro-2-thiophenecarboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 11229445tert-Butyl 3-amino-4-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 74835283tert. Butyl (3SR,4SR)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-hydroxy-pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

201 mg (1.2 mmol) 5-chlorothiophene-2-carboxylic acid and 436 mg (1.4 mmol) TBTU are suspended in 5 ml DCM and combined with 260 μl (1.9 mmol) TEA. The mixture is stirred for 30 minutes and then a solution of 250 mg (1.2 mmol) tert. Butyl (3SR,4SR)-3-amino-4-hydroxy-pyrrolidine-1-carboxylate in 5 ml DCM is added and the mixture is stirred for 16 hours at RT. Then the reaction mixture is poured into water and extracted with DCM. The organic phase is washed with sat. sodium chloride solution and, after being mixed with activated charcoal, dried on sodium sulphate. The mixture is filtered and the filtrate is evaporated to dryness. The residue thus obtained is purified by column chromatography (silica gel, eluant DCM/MeOH 10:1).

Workup

  1. stirringthe mixture is stirred for 16 hours at RT
  2. extractionextracted with DCM
  3. washThe organic phase is washed with sat. sodium chloride solution
  4. additionafter being mixed with activated charcoal
  5. customdried on sodium sulphate
  6. filtrationThe mixture is filtered
  7. customthe filtrate is evaporated to dryness
  8. customThe residue thus obtained
  9. customis purified by column chromatography (silica gel, eluant DCM/MeOH 10:1)

Sources & evidence

ORD record
ord-ac3d6ee1ae6d4d22b9676ccfd73faca3
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08309542B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes