Water → (2s,3s)-5-{2-[(5-{[(Benzyloxy)carbonyl]amino}pentyl)amino]-2-oxoethyl}-2-[(3-phenylpyrrolidin-1-yl)carbonyl]piperidine-3-carboxylic acid

HRID 61431Notes

Reaction equation

HRID 61431 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:46])[CH2:19][CH:20]1[CH2:25][NH:24][C@H:23]([C:26]([N:28]2[CH2:32][CH2:31][CH:30]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:29]2)=[O:27])[C@@H:22]([C:39]([O:41]C(C)(C)C)=[O:40])[CH2:21]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:46])[CH2:19][CH:20]1[CH2:25][NH:24][C@H:23]([C:26]([N:28]2[CH2:32][CH2:31][CH:30]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH2:29]2)=[O:27])[C@@H:22]([C:39]([OH:41])=[O:40])[CH2:21]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 67304960Tert-butyl (2s,3s)-5-{2-[(5-{[(benzyloxy)carbonyl]amino}pentyl)amino]-2-oxoethyl}-2-[(3-phenylpyrrolidin-1-yl)carbonyl]piperidine-3-carboxylate

Product 1

HCID 67304154(2s,3s)-5-{2-[(5-{[(Benzyloxy)carbonyl]amino}pentyl)amino]-2-oxoethyl}-2-[(3-phenylpyrrolidin-1-yl)carbonyl]piperidine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl(2S,3S)-5-{2-[(5-{[(benzyloxy)carbonyl]amino}pentyl)amino]-2-oxoethyl}-2[(3-phenylpyrrolidin-1-yl)carbonyl]piperidine-3-carboxylate (40 mg, 0.063 mmol) in methylene chloride (2 mL) was added a drop of water and trifluoroacetic acid (4 mL). After stirring the reaction mixture overnight, the volatiles were removed in-vacuo and the residue was azeotropically washed with benzene (2×3 mL) and heptane (2×3 mL). The crude product was dried under high vacuum and used directly in the following coupling reaction without purification. MS (ESI): 579 (M+H).

Workup

  1. customthe volatiles were removed in-vacuo
  2. washthe residue was azeotropically washed with benzene (2×3 mL) and heptane (2×3 mL)
  3. dry with materialThe crude product was dried under high vacuum
  4. customused directly in the following coupling reaction without purification

Sources & evidence

ORD record
ord-da6e3da6d34240bf8124b65a1654f4c6
Source dataset
uspto-grants-2016_09
Patent number
US09440958B2

Reaction notes

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