Hydrochloric Acid → Boc-(D)Phe-Pro-OBzl

HRID 1648383Notes

Reaction equation

HRID 1648383 reaction equation
[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@@H:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH:20]1[CH2:34][CH2:33][CH2:32][C@H:21]1[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23].Cl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)C(C)C)(C)C.CN(C)CCCN=C=NCC.Cl>ClCCl.C(OCC)C>[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@@H:2]([C:10]([N:20]1[CH2:34][CH2:33][CH2:32][C@H:21]1[C:22]([O:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:23])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 637610Boc-D-phenylalanineHCID 2733413Proline benzyl ester hydrochloride

Product 1

HCID 11155205Boc-(D)Phe-Pro-OBzl

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of Boc-D-Phe-OH (89.1 g, 336 mmol), Pro-OBzl.HCl (81.2g, 336 mmol), HOBT (50 g, 370 mmol) and N,N-diisopropylethylamine (176 mL, 1,008 mmol) at 0° C. in dichloromethane (600 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide.HCl (71 g, 370 mmol). After stirring for 18 h, the mixture was diluted with diethyl ether 1 L) and washed three times with 1N citric acid (250 mL), once with water (250 mL), three times with sat'd aqueous NaHCO3 (250 mL) and once with sat'd aqueous NaCl (250 mL). The organic phase was dried (Na2SO4), filtered, and concentrated in vacuo to yield 140 g (92.5%) of a pale yelow foam.

Workup

  1. washwashed three times with 1N citric acid (250 mL)
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto yield 140 g (92.5%) of a pale yelow foam

Sources & evidence

ORD record
ord-396d6fca44e1482c8a7fb85183f76a44
Source dataset
uspto-grants-1995_07
Patent number
US05436229

Reaction notes

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