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Ammonium Chloride → HCID 68646427, compound

HRID 1162641
Notes
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Reaction equation

HRID 1162641 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C:11](=O)[C@@H:10]([NH:14][C:15]([C:17]2[S:18][C:19]([Cl:22])=[CH:20][CH:21]=2)=[O:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+].CC[N:27](C(C)C)C(C)C.[BH4-].[Na+]>CCO.CCOC(C)=O.CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]([NH:14][C:15]([C:17]2[S:18][C:19]([Cl:22])=[CH:20][CH:21]=2)=[O:16])[C@@H:11]([NH2:27])[CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 4311764Sodium borohydrideHCID 58748273HCID 58748273, compound

Product 1

HCID 68646427HCID 68646427, compound

Reagents, catalysts & solvents 3

HCID 11026
Titanium isopropoxide
Catalyst
HCID 702EthanolSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

35.2 A solution of 500 mg (S)-3-[(5-chloro-thiophene-2-carbonyl)-amino]-4-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester in 20 ml EtOH was treated with 155 mg ammonium chloride, 0.49 ml Hünig's base and 0.86 ml tetraisopropyl orthotitanate. The reaction mixture was stirred for 5 hrs at 40° C. Then it was cooled to 0° C., treated with 110 mg NaBH4 and stirred at r.t. overnight. The mixture was diluted with EtOAc and washed with H2O. The organic layer was dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (silica gel, gradient: CH2Cl2->CH2Cl2/MeOH 9:1) to give 180 mg (S)-3-amino-4-[(5-chloro-thiophene-2-carbonyl)-amino]-pyrrolidine-1-carboxylic acid tert-butyl ester as yellow solid. MS 344.3 ([M−H]−)

Workup

  1. temperatureThen it was cooled to 0° C.
  2. stirringstirred at r.t. overnight
  3. washwashed with H2O
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography (silica gel, gradient: CH2Cl2->CH2Cl2/MeOH 9:1)

Sources & evidence

ORD record
ord-a906de0c652b4c3ab6b3062fe3a28279
Source dataset
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07820699B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes