Trifluoroacetic acid methylene chloride → N-[5-({N-acetyl-4-[(carboxycarbonyl)(2-carboxyphenyl)amino]-3-ethylphenylalanyl}amino)pentanoyl]-L-tyrosine

HRID 488644Notes

Reaction equation

HRID 488644 reaction equation
[C:1]([NH:4][CH:5]([CH2:32][C:33]1[CH:38]=[CH:37][C:36]([N:39]([C:62](=[O:70])[C:63]([O:65]C(C)(C)C)=[O:64])[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=2[C:46]([O:48]C(C2C=CC=CC=2)C2C=CC=CC=2)=[O:47])=[C:35]([CH2:71][CH3:72])[CH:34]=1)[C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([NH:15][C@@H:16]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27]C(C)(C)C)=[CH:23][CH:22]=1)[C:17]([OH:19])=[O:18])=[O:14])=[O:7])(=[O:3])[CH3:2].FC(F)(F)C(O)=O.ClCCl>>[C:1]([NH:4][C@H:5]([C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([NH:15][C@H:16]([C:17]([OH:19])=[O:18])[CH2:20][C:21]1[CH:22]=[CH:23][C:24]([OH:27])=[CH:25][CH:26]=1)=[O:14])=[O:7])[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([N:39]([C:62]([C:63]([OH:65])=[O:64])=[O:70])[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=2[C:46]([OH:48])=[O:47])=[C:35]([CH2:71][CH3:72])[CH:34]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 86585322(2S)-2-[(5-{[2-(acetylamino)-3-(4-{2-[(benzhydryloxy)carbonyl][tert-butoxy(oxo)acetyl]anilino}-3-ethylphenyl)propanoyl]amino}pentanoyl)amino]-3-(4-tert-butoxyphenyl)propanoic acid

Product 1

HCID 10122867N-[5-({N-acetyl-4-[(carboxycarbonyl)(2-carboxyphenyl)amino]-3-ethylphenylalanyl}amino)pentanoyl]-L-tyrosine

Procedure

(2S)-2-[(5-{[2-(acetylamino)-3-(4-{2-[(benzhydryloxy)carbonyl][tert-butoxy(oxo)acetyl]anilino}-3-ethylphenyl)propanoyl]amino}pentanoyl)amino]-3-(4-tert-butoxyphenyl)propanoic acid was treated with trifluoroacetic acid/dichloromethane (1 mL, 1:1) at ambient temperature for 3 hours, concentrated under reduced pressure and purified by HPLC eluting with 5-100% acetonitrile/aqueous 0.1% trifluoroacetic acid to provide the titled compound. MS (ESI(+)) m/e 705 (M+H)+; 1H NMR (500 MHz, DMSO-d6) δ 12-13.5 (bs, 2H), 9.18 (s, 1H), 8.11-7.78 (m, 4H), 7.59-6.98 (m, 7H), 6.80-6.61 (m, 3H), 4.57-4.40 (m, 1H), 4.39-4.32 (m, 1H), 3.00-2.55 (m, 6H), 2.04-2.00 (m, 2H), 1.78, 1.75 (s, s, 3H), 1.40-1.36 (m, 2H), 1.35-1.20 (m, 2H), 1.35-0.91 (m, 3H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. custompurified by HPLC
  3. washeluting with 5-100% acetonitrile/aqueous 0.1% trifluoroacetic acid

Sources & evidence

ORD record
ord-15daa06d92204488842245883d917b51
Source dataset
uspto-grants-2005_12
Patent number
US06972340B2

Reaction notes

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