Water → (2S,4S)-1-(1-Carbamoyl-1H-indol-3-ylcarbamoyl)-4-(9H-fluoren-9-ylmethoxy carbonylamino)-pyrrolidine-2-carboxylic acid benzyl ester

HRID 1527375Notes

Reaction equation

HRID 1527375 reaction equation
[CH2:1]([O:8][C:9]([C@@H:11]1[CH2:15][C@H:14]([NH:16][C:17]([O:19][CH2:20][CH:21]2[C:33]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:27]3[C:22]2=[CH:23][CH:24]=[CH:25][CH:26]=3)=[O:18])[CH2:13][NH:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(CC)CC.[N:41]([C:44]1[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[N:46]([C:53]([NH2:55])=[O:54])[CH:45]=1)=[C:42]=[O:43].O>C1COCC1>[CH2:1]([O:8][C:9]([C@@H:11]1[CH2:15][C@H:14]([NH:16][C:17]([O:19][CH2:20][CH:21]2[C:33]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:27]3[C:22]2=[CH:23][CH:24]=[CH:25][CH:26]=3)=[O:18])[CH2:13][N:12]1[C:42](=[O:43])[NH:41][C:44]1[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[N:46]([C:53](=[O:54])[NH2:55])[CH:45]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 575200853-Isocyanato-indole-1-carboxylic acid amideHCID 68283582(2S,4S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-pyrrolidine-2-carboxylic acid benzyl ester

Product 1

HCID 68283841(2S,4S)-1-(1-Carbamoyl-1H-indol-3-ylcarbamoyl)-4-(9H-fluoren-9-ylmethoxy carbonylamino)-pyrrolidine-2-carboxylic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (2S,4S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-pyrrolidine-2-carboxylic acid benzyl ester (3.03 g, 5.45 mmol) and Et3N (1.1 mL, 8.2 mmol) in dry THF (60 mL) was added a solution of 3-isocyanato-indole-1-carboxylic acid amide (1.1 g, 5.4 mmol, prepared as described in Scheme A1) in dry THF (60 mL). The resulting solution was stirred at RT under nitrogen for 20 min. The mixture was poured into water and extracted twice with EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated under high vacuum (the temperature of the water bath of the rotary evaporator was kept to RT) to give the title compound. Rf (c-hexane/EtOAc 1:3)=0.39; MS (LCMS): 644.2 [M+H]+, 666.2 [M+Na]+; tR (HPLC conditions a): 4.0 min.

Workup

  1. extractionextracted twice with EtOAc
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under high vacuum (
  5. customthe temperature of the water bath of the rotary evaporator
  6. customwas kept to RT

Sources & evidence

ORD record
ord-d68aee41e3f24204a3745942f604f307
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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